JP2005350365A - Composition for lip - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a composition for lips excellent in cosmetic retention and improved in covering feelings on lips. <P>SOLUTION: This composition for lips comprises a copolymer comprising as constituent monomers an acrylic acid monomer (A), a polyoxyalkylene group-containing monomer (B) and an organopolysiloxane-containing monomer (C) where the content of the monomer (A) is at least 20 mass% based on the total weight of the constituent monomers. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a composition for lips, in particular, improvement of makeup retention and improvement of the coating feeling on the lips.

  Conventionally, normal oily lipsticks are composed of various oils, waxes, coloring materials, etc., and when applied to the lips, the gloss is good, but the color may transfer to coffee cups, clothing, etc. There was a problem that the color faded and the makeup lasting was bad.

  Various studies have been made in the past in order to improve such problems with makeup. For example, lipsticks using various silicones such as alkylmethylpolysiloxane, polyoxyalkylene-modified organopolysiloxane, trimethylsiloxysilicic acid, and non-aqueous polymer dispersion as a film forming component have been proposed (for example, patent documents) 1-6).

  However, lipsticks formulated with these film-forming components have a certain level of function in terms of gloss and make-up, but cause a feeling of film on the lips due to the film-forming components of the raw material. There was a problem in terms of use feeling. On the other hand, when the blending amount of the film forming component is reduced, the film feeling on the lips is good, but the effect of improving the longevity cannot be obtained sufficiently, and it is very difficult to perform both functions at the same time. It was a problem.

Japanese Patent Laid-Open No. 5-178722 JP-A-6-298623 Japanese Patent Laid-Open No. 7-33622 Japanese Examined Patent Publication No. 61-1284 JP-A-8-225432 JP-A-10-59827

  The present invention has been made in view of the above-described problems, and an object of the present invention is to provide a composition for lips that is excellent in long-lasting makeup and has an improved coating feeling on the lips.

  As a result of intensive studies in view of the aforementioned problems, the present inventors have found that a copolymer polymer containing an acrylic acid monomer, a polyoxyalkylene group-containing monomer, and an organopolysiloxane-containing monomer at a specific ratio is obtained. By blending in the lip composition as a film-forming component, it has excellent makeup durability and the coating feeling on the lips is remarkably improved as compared with the case where a conventional film-forming component is used. As a result, the present invention has been completed.

（上記式中、Ｒ^１は水素、又は炭素数１〜３の炭化水素基を表し、Ｒ^２は水素、又は炭素数１〜２４の炭化水素基を表す。）

（上記式中、Ｒ^３は水素、又は炭素数１〜３の炭化水素基、Ｒ^４は炭素数１〜４の２価炭化水素基、Ｒ^５は水素、又は炭素数１〜２４の炭化水素基を表し、ｌは１〜５０の整数を表す。）

（上記式中、Ｒ^６は水素、又は炭素数１〜３の炭化水素基、Ｒ^７は炭素数１〜４の２価炭化水素基、Ｒ^８は炭素数１〜６の炭化水素基を表し、ｍは０〜５００、ｎは１〜３の整数を表す。） That is, the composition for lips according to the present invention is represented by the monomer (A) represented by the following general formula (1), the monomer (B) represented by the following general formula (2), and the following general formula (3). The monomer (C) is contained as a constituent monomer, and the content of the monomer (A) is a copolymer polymer that is 20% by mass or more based on the total amount of the constituent monomers.

(In the above formula, R ¹ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, and R ² represents hydrogen or a hydrocarbon group having 1 to 24 carbon atoms.)

(In the above formula, R ³ is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁴ is a divalent hydrocarbon group having 1 to ⁴ carbon atoms, R ⁵ is hydrogen or a hydrocarbon having 1 to 24 carbon atoms. Represents a group, and l represents an integer of 1 to 50.)

(In the above formula, R ⁶ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁷ represents a divalent hydrocarbon group having 1 to 4 carbon atoms, and R ⁸ represents a hydrocarbon group having 1 to 6 carbon atoms. M represents 0 to 500, and n represents an integer of 1 to 3.)

（上記式中、ｘは０〜３の整数を表す。）

（上記式中、ｙは３〜６の整数を表す。）

（上記式中、Ｒ^９は炭素数２〜８の炭化水素基を表す。） In the lip composition, a linear silicone oil represented by the following general formula (4), a cyclic silicone oil represented by the following general formula (5), and an alkyl-modified silicone oil represented by the following general formula (6) It is preferable to contain one or more volatile oils selected from among isoparaffins.

(In the above formula, x represents an integer of 0 to 3.)

(In the above formula, y represents an integer of 3 to 6.)

(In the above formula, R ⁹ represents a hydrocarbon group having 2 to 8 carbon atoms.)

（式中、ｏ，ｐは平均数で、ｏは１〜１５０、ｐは０〜１５０の整数を表し、ｏ，ｐの総和は４以上であり、ａは０〜１０の整数、Ｒ^１０は炭素数１〜１２のパーフロロアルキル基を表す。）

（式中、ｑ，ｒ，ｓは平均数で、ｑは１〜１５０、ｒは１〜１５０、ｓは０〜１５０の整数を表し、ｑ，ｒ，ｓの総和は４以上であり、ｂは０〜１０の整数、Ｒ^１１、Ｒ^１２はメチル基、あるいはフェニル基を表し、Ｒ^１１、Ｒ^１２のうち少なくとも１つがフェニル基であり、Ｒ^１３は炭素数１〜１２のパーフロロアルキル基を表す。）

（式中、ＯＲ^１４は炭素数２〜３０のアルコキシ基を、ｔ、ｕは平均数で、ｔは１〜５００、ｕは０〜５００の整数を表し、ｔ，ｕの総和は４以上である。）

（式中、Ｒ^１５は炭素数１０〜３０のアルキル基を、ｖ、ｗは平均数で、ｖは１〜５００、ｗは０〜５００の整数を表し、ｖ，ｗの総和は４以上である。）
また、前記口唇用組成物において、さらに水及び／又は保湿剤を含有することが好適である。 In the lip composition, the fluorine-modified dimethyl silicone represented by the following general formula (7), the fluorine-modified phenyl silicone represented by the following general formula (8), and the alkoxy-modified silicone represented by the following general formula (9) One or more non-volatile oils selected from alkyl-modified silicones represented by the following general formula (10), tri (hydrogenated rosin / isostearic acid) glyceryl, and 2-methoxyhexyl paramethoxycinnamate It is preferable to contain.

(Wherein, o and p are average numbers, o is an integer of 1 to 150, p is an integer of 0 to 150, the sum of o and p is 4 or more, a is an integer of 0 to ¹⁰ , and R ¹⁰ is Represents a perfluoroalkyl group having 1 to 12 carbon atoms.)

(In the formula, q, r, and s are average numbers, q is 1 to 150, r is 1 to 150, s is an integer of 0 to 150, and the sum of q, r, and s is 4 or more, b Is an integer of 0 to 10, R ¹¹ and R ¹² represent a methyl group or a phenyl group, at least one of R ¹¹ and R ¹² is a phenyl group, and R ¹³ is a perfluoroalkyl group having 1 to 12 carbon atoms. Represents.)

(In the formula, OR ¹⁴ represents an alkoxy group having 2 to 30 carbon atoms, t and u are average numbers, t represents 1 to 500, u represents an integer of 0 to 500, and the sum of t and u is 4 or more. is there.)

(In the formula, R ¹⁵ represents an alkyl group having 10 to 30 carbon atoms, v and w are average numbers, v represents 1 to 500, w represents an integer of 0 to 500, and the sum of v and w is 4 or more. is there.)
The lip composition preferably further contains water and / or a humectant.

  The composition for lips according to the present invention is extremely superior in makeup lasting as compared with conventional lip compositions, and has a coating feeling on the lips, by incorporating a copolymer polymer having a specific structure. Is significantly improved.

（上記式中、Ｒ^１は水素、又は炭素数１〜３の炭化水素基を表し、Ｒ^２は水素、又は炭素数１〜２４の炭化水素基を表す。）

（上記式中、Ｒ^３は水素、又は炭素数１〜３の炭化水素基、Ｒ^４は炭素数１〜４の２価炭化水素基、Ｒ^５は水素、又は炭素数１〜２４の炭化水素基を表し、ｌは１〜５０の整数を表す。）

（上記式中、Ｒ^６は水素、又は炭素数１〜３の炭化水素基、Ｒ^７は炭素数１〜４の２価炭化水素基、Ｒ^８は炭素数１〜６の炭化水素基を表し、ｍは０〜５００、ｎは１〜３の整数を表す。） Hereinafter, preferred embodiments of the present invention will be described in detail.
The copolymer polymer used in the lip composition according to the present invention includes a monomer (A) represented by the following general formula (1), a monomer (B) represented by the following general formula (2), and the following general formula: The monomer (C) represented by (3) is contained as a constituent monomer, and the content of the monomer (A) is adjusted so as to be 20% by mass or more based on the total amount of the constituent monomers.

(In the above formula, R ¹ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, and R ² represents hydrogen or a hydrocarbon group having 1 to 24 carbon atoms.)

(In the above formula, R ³ is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁴ is a divalent hydrocarbon group having 1 to ⁴ carbon atoms, R ⁵ is hydrogen or a hydrocarbon having 1 to 24 carbon atoms. Represents a group, and l represents an integer of 1 to 50.)

(In the above formula, R ⁶ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁷ represents a divalent hydrocarbon group having 1 to 4 carbon atoms, and R ⁸ represents a hydrocarbon group having 1 to 6 carbon atoms. M represents 0 to 500, and n represents an integer of 1 to 3.)

The monomer (A) represented by the general formula (1) is an alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid, or an alkyl ester thereof. In the general formula (1), R ¹ is a substituent of acrylic acid α carbon is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R ¹ is particularly preferably hydrogen or a methyl group. In the general formula (1), R ² is a terminal substituent of acrylic acid is hydrogen or a hydrocarbon group having 1 to 24 carbon atoms. Examples of the hydrocarbon group include an alkyl group and an alkenyl group, which may be linear or branched and may be partially substituted with a hydroxyl group or a fluorine atom. Examples of R ² include a hydrogen atom, methyl group, ethyl group, propyl group, butyl group, hexyl group, 2-ethylhexyl group, decyl group, tridecyl group, stearyl group, isostearyl group, 2-hydroxyethyl group, 2 -A hydroxypropyl group, a trifluoromethyl group, a trifluoroethyl group, etc. are mentioned. Particularly preferred are a hydrogen atom, a methyl group, a butyl group, a 2-ethylhexyl group, a tridecyl group, a stearyl group, and an isostearyl group.

Examples of the monomer (A) used in the present invention include acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, decyl acrylate, and lauryl acrylate. , Alkyl acrylates such as stearyl acrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, decyl methacrylate, dodecyl methacrylate, methacrylic acid Examples include methacrylic acid alkyl esters such as tridecyl, stearyl methacrylate, and isostearyl methacrylate.
In the copolymer polymer used in the present invention, one or more of the monomers (A) can be used as a constituent monomer.

  In the copolymer used in the present invention, the content of the monomer (A) needs to be 20% by mass or more based on the total amount of the constituent monomers. When the content of the monomer (A) is less than 20% by mass with respect to the total amount of the constituent monomers, the film forming ability may be lowered. Moreover, it is suitable that content of a monomer (A) is 20-60 mass%, Most preferably, it is 25-50 mass%.

The monomer (B) represented by the general formula (2) is a compound having an oxyalkylene moiety in an alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid. For example, an alkylene glycol of acrylic acid or alkyl-substituted acrylic acid Esters or their alkyl ethers. In general formula (2), R ³ is a substituent of acrylic acid α carbon is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R ³ is particularly preferably hydrogen or a methyl group. In the general formula (2), R ⁴ is a hydrocarbon moiety in the oxyalkylene group is a divalent hydrocarbon group having 1 to 4 carbon atoms. Examples of the divalent hydrocarbon group include an alkylene group, which may be linear or branched. R ⁴ may be the same or different. For example, the oxyalkylene moiety is a block-like or random repeating structure composed of two or more oxyalkylene groups having R ⁴ having different carbon numbers. Also good. The R ^4, and particularly preferably an ethylene group. In the general formula (2), R ⁵ is a terminal substituent of the oxyalkylene group is hydrogen or a hydrocarbon group having 1 to 24 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R ⁵ is hydrogen, particularly preferably a methyl group. Moreover, in General formula (2), l showing the number of repeating units of an oxyalkylene group is an integer of 1-50. l is particularly preferably 1-20.

The monomer (B) for use in the present invention, _{e.g., CH 2 = C (CH 3} ) COO (C 2 H 4 O) 6 H, CH 2 = C (CH 3) COO (C 2 H 4 O) 8 _{H, CH 2 = C (CH} 3) COO (C 2 H 4 O) 10 H, CH 2 = C (CH 3) COO (C 2 H 4 O) 15 H, CH 2 = C (CH 3) COO ( _{C 2 H 4 O) 6 CH} 3, CH 2 = C (CH 3) COO (C 2 H 4 O) 8 CH 3, CH 2 = C (CH 3) COO (C 2 H 4 O) 10 CH 3, _{CH 2 = C (CH 3)} COO (C 2 H 4 O) 15 C 4 H 9, CH 2 = CHCOO (C 2 H 4 O) 6 H, CH 2 = CHCOO (C 2 H 4 O) 8 H, _{CH 2 = CHCOO (C 2 H} 4 O) 10 H, CH 2 = CHCOO (C 2 H _{O) 15 H, CH 2 =} CHCOO (C 2 H 4 O) 6 CH 3, CH 2 = CHCOO (C 2 H 4 O) 8 CH 3, CH 2 = CHCOO (C 2 H 4 O) 10 CH 3, _{CH 2 = CHCOO (C 2 H} 4 O) 15 C 4 H 9, CH 2 = CHCOO (C 2 H 4 O) 10 (C 3 H 6 O) 10 C 12 H 25, CH 2 = C (CH 3) _{COO (C 2 H 4 O)} 30 (C 3 H 6 O) 10 C 18 H 37 , and the like.
In the copolymer polymer used in the present invention, one or more of the monomers (B) can be used as a constituent monomer.

  In the copolymer used in the present invention, the content of the monomer (B) is not particularly limited, but is preferably 0.1 to 50% by mass with respect to the total amount of the constituent monomers. . When the content of the monomer (B) is less than 0.1% by mass with respect to the total amount of the constituent monomers, the film feeling may become strong, and when it exceeds 50% by mass, the film forming ability may be lowered. Moreover, it is especially suitable that content of a monomer (B) is 1-40 mass%.

The monomer (C) represented by the general formula (1) is a compound having an organopolysiloxane moiety in alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid. For example, acrylic acid or alkyl-substituted acrylic acid An ester in which an organopolysiloxane is linked via a divalent hydrocarbon group. In general formula (3), R ⁶ representing a substituent acrylic acid α carbon is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R ⁶ is particularly preferably hydrogen or a methyl group. In the general formula (3), R ⁷ is a hydrocarbon group linking sites acrylic acid and organopolysiloxane site is a divalent hydrocarbon group having 1 to 4 carbon atoms. Examples of the divalent hydrocarbon group include an alkylene group, which may be linear or branched. R ⁷ is particularly preferably a propylene group. In the general formula (3), R ⁸ is the side chain substituent groups of the organopolysiloxane group is a hydrocarbon group having 1 to 6 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, a fluoroalkyl group, and the like, and may be either linear or branched. R ⁸ may be the same or different. For example, only a part of terminal R ⁸ may be a hydrocarbon group having a different carbon number. R ⁸ is particularly preferably a methyl group, a phenyl group, or a trifluoropropyl group. Moreover, in General formula (3), m showing the repeating unit number of an organosiloxy group is an integer of 0-500. m is particularly preferably 0 to 200. Moreover, in General formula (3), n showing the substitution frequency of an organosiloxy group is an integer of 1-3.

As the monomer (C) used in the present invention, for _{example, CH 2 = C (CH 3} ) COOC 3 H 6 Si {OSi (CH 3) 3} 3, CH 2 = C (CH 3) COOC 3 H 6 { _{Si (CH 3) 2 O}} 20 Si (CH 3) 3, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 40 Si (CH 3) 2 C 4 H 9, CH _{2 = C (CH 3) COOC} 3 H 6 {Si (CH 3) 2 O} 100 Si (CH 3) 2 C 4 H 9, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) _{2 O} 100 {Si (C} 6 H 5) 2 O} 20 Si (CH 3) 2 C 4 H 9, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 150 { _{Si (CH 3) (C 2} H 4 CF 3) O _{50 Si (CH 3) 2 C} 4 H 9 and the like.
In the copolymer polymer used in the present invention, one or more of the monomers (C) can be used as a constituent monomer.

  In the copolymer used in the present invention, the content of the monomer (C) is not particularly limited, but is preferably 30 to 80% by mass with respect to the total amount of the constituent monomers. When the content of the monomer (C) is less than 30% by mass relative to the total amount of the constituent monomers, the solubility with the silicone component may deteriorate in the formulation, and when it exceeds 80% by mass, the film forming ability is low. There is a case. Moreover, it is especially suitable that content of a monomer (C) is 40-70 mass%.

  Moreover, if it is a range which does not impair the effect of this invention, monomers other than said (A)-(C) can also be contained as a constituent monomer. Content should just be the range of 50 mass% or less of a constituent monomer total amount, for example, can contain about 0.0001-10 mass%. Examples of such monomers include ethylene, propylene, butadiene, styrene, vinyl chloride, vinylidene chloride, vinyl alcohol, vinyl acetate, maleic anhydride, acrylonitrile, acrylamide, methacrylamide, methyl acrylamide, methyl methacrylamide, dimethyl methacrylamide. , Ethylacrylamide, ethylmethacrylamide, diethylmethacrylamide, N-isopropylacrylamide, N-vinylpyrrolidone, ε-caprolactam, N, N′-dimethylaminoethylmethacrylic acid, diallyldimethylammonium chloride, 2-acrylamido-2-methylpropane Examples thereof include sodium sulfonate.

  The copolymer used for this invention can be obtained by superposing | polymerizing using the said monomer (A)-(C) using a well-known polymerization method. As the polymerization method, for example, a homogeneous solution polymerization method, a heterogeneous solution polymerization method, an emulsion polymerization method, a reverse phase emulsion polymerization method, a bulk polymerization method, a suspension polymerization method, a precipitation polymerization method and the like can be used. For example, in the case of homogeneous solution polymerization, the monomers (A) to (C) are dissolved in a solvent with an appropriate monomer composition, and a radical polymerization initiator is added and stirred under heating in a nitrogen atmosphere. Can be obtained. A copolymer can also be obtained by a post-modification method using polyacrylic acid and adding an appropriate functional group later.

  As the solvent used in the polymerization, any solvent can be used as long as it can dissolve or suspend each monomer. For example, alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, and butyl alcohol can be used. Solvents, hexane, heptane, octane, isooctane, decane, liquid solvents such as liquid paraffin, ether solvents such as dimethyl ether, diethyl ether, tetrahydrofuran, ketone solvents such as acetone, methyl ethyl ketone, methyl acetate, ethyl acetate, acetic acid In addition to ester solvents such as butyl and chloride solvents such as methylene chloride, chloroform and carbon tetrachloride, dimethylformamide, diethylformamide, dimethylsulfoxide, dioxane and the like can be mentioned. Two or more of these solvents may be mixed and used. Usually, it is suitable to select a solvent having a boiling point higher than the starting temperature of the polymerization initiator to be used.

  The polymerization initiator is not particularly limited as long as it has the ability to initiate radical polymerization. For example, peroxide such as benzoyl peroxide, azobisisobutyronitrile (AIBN), 2,2′-azobis (Isobutyric acid) In addition to azo compounds such as dimethyl, persulfuric acid polymerization initiators such as potassium persulfate and ammonium persulfate may be mentioned. In addition, it can superpose | polymerize also by photochemical reaction, radiation irradiation, etc. irrespective of these polymerization initiators. The polymerization temperature is not less than the polymerization start temperature of each polymerization initiator. For example, in the case of a peroxide-based polymerization initiator, it may be usually about 70 ° C.

  The polymerization time is not particularly limited, but is usually 2 to 24 hours. When it is desired to obtain a relatively high molecular weight polymer, it is desirable to react for about one day. If the reaction time is too short, unreacted monomers may remain and the molecular weight may be relatively small. The average molecular weight of the copolymer used in the present invention is not particularly limited, but in particular, the average molecular weight is preferably about 10,000 to 200,000. In addition, in the copolymer molecule used in the present invention, the order in which the monomers (A) to (C) are added is not particularly specified, and even if they are added in blocks, they are added randomly. However, usually, a copolymer in which the monomers (A) to (C) are randomly added can be obtained.

An example of a typical copolymer used in the present invention is shown in the following general formula (11).

In the general formula (11), R ^{1 to} R ⁸ , l, m, and n are as defined above. a, b, and c represent the mass proportions of the monomer (A), monomer (B), and monomer (C) in the total amount of the constituent monomers. In the general formula (11), “a” representing the mass ratio of the monomer (A) to the total amount of the constituent monomers is adjusted to 20% by mass or more.

  In the composition for lips according to the present invention, the blending amount of the copolymer polymer is not particularly limited and can be used by appropriately adjusting the blending amount according to the purpose of use, but the total amount of the composition The content is preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass. When the amount of the copolymer is less than 0.1% by mass, the effect of improving the longevity of the makeup may not be recognized. On the other hand, when it is more than 20% by mass, a remarkable film feeling is felt on the lips. There is a case.

The present invention improves the cosmetic durability of the lip composition and improves the coating feeling on the lip by blending the copolymer polymer produced as described above into the lip composition. It is.
In the composition for lips according to the present invention, in addition to the copolymer polymer which is an essential component, components usually used in cosmetics and pharmaceuticals can be blended within a range not impairing the effects of the present invention.

（上記式中、ｘは０〜３の整数を表す。）

（上記式中、ｙは３〜６の整数を表す。）

（上記式中、Ｒ^９は炭素数２〜８の炭化水素基を表す。） For example, in the composition for lips according to the present invention, a volatile oil can be suitably blended together with the copolymer. The volatile oil used in the present invention includes a linear silicone oil represented by the following general formula (4), a cyclic silicone oil represented by the following general formula (5), and an alkyl-modified silicone represented by the following general formula (6). Examples include oil and isoparaffin.

(In the above formula, x represents an integer of 0 to 3.)

(In the above formula, y represents an integer of 3 to 6.)

(In the above formula, R ⁹ represents a hydrocarbon group having 2 to 8 carbon atoms.)

  In the composition for lips according to the present invention, one or more volatile oil components may be selected and blended. The blending amount of the volatile oil is not particularly limited, but is preferably 10 to 90% by mass, and more preferably 20 to 80% by mass in the composition. If the blending amount of the volatile oil is too small, makeup may be deteriorated, and if it is too much, the shape stability of the lipstick may be deteriorated.

（式中、ｏ，ｐは平均数で、ｏは１〜１５０、ｐは０〜１５０の整数を表し、ｏ，ｐの総和は４以上であり、ａは０〜１０の整数、Ｒ^１０は炭素数１〜１２のパーフロロアルキル基を表す。）

（式中、ｑ，ｒ，ｓは平均数で、ｑは１〜１５０、ｒは１〜１５０、ｓは０〜１５０の整数を表し、ｑ，ｒ，ｓの総和は４以上であり、ｂは０〜１０の整数、Ｒ^１１、Ｒ^１２はメチル基、あるいはフェニル基を表し、Ｒ^１１、Ｒ^１２のうち少なくとも１つがフェニル基であり、Ｒ^１３は炭素数１〜１２のパーフロロアルキル基を表す。）

（式中、ＯＲ^１４は炭素数２〜３０のアルコキシ基を、ｔ、ｕは平均数で、ｔは１〜５００、ｕは０〜５００の整数を表し、ｔ，ｕの総和は４以上である。）

（式中、Ｒ^１５は炭素数１０〜３０のアルキル基を、ｖ、ｗは平均数で、ｖは１〜５００、ｗは０〜５００の整数を表し、ｖ，ｗの総和は４以上である。） Moreover, in the composition for lips according to the present invention, a non-volatile oil can be suitably blended. Nonvolatile oils used in the present invention include fluorine-modified dimethyl silicone represented by the following general formula (7), fluorine-modified phenyl silicone represented by the following general formula (8), and alkoxy modification represented by the following general formula (9). Examples include silicone, alkyl-modified silicone represented by the following general formula (10), tri (hydrogenated rosin / isostearic acid) glyceryl, and 2-methoxyhexyl paramethoxycinnamate.

(Wherein, o and p are average numbers, o is an integer of 1 to 150, p is an integer of 0 to 150, the sum of o and p is 4 or more, a is an integer of 0 to ¹⁰ , and R ¹⁰ is Represents a perfluoroalkyl group having 1 to 12 carbon atoms.)

(In the formula, q, r, and s are average numbers, q is 1 to 150, r is 1 to 150, s is an integer of 0 to 150, and the sum of q, r, and s is 4 or more, b Is an integer of 0 to 10, R ¹¹ and R ¹² represent a methyl group or a phenyl group, at least one of R ¹¹ and R ¹² is a phenyl group, and R ¹³ is a perfluoroalkyl group having 1 to 12 carbon atoms. Represents.)

(In the formula, OR ¹⁴ represents an alkoxy group having 2 to 30 carbon atoms, t and u are average numbers, t represents 1 to 500, u represents an integer of 0 to 500, and the sum of t and u is 4 or more. is there.)

(In the formula, R ¹⁵ represents an alkyl group having 10 to 30 carbon atoms, v and w are average numbers, v represents 1 to 500, w represents an integer of 0 to 500, and the sum of v and w is 4 or more. is there.)

  In the composition for lips according to the present invention, one or more of the non-volatile oils may be selected and blended. The compounding amount of the non-volatile oil component is preferably 0.1 to 50% by mass, more preferably 0.5 to 40% by mass in the composition. If the blended amount of the non-volatile oil is too small, the feeling of use may be poor, and if it is too large, the makeup may be deteriorated.

  In the lip composition according to the present invention, water or a humectant can be suitably blended. Examples of the humectant used in the present invention include ethylene glycol, diethylene glycol, 1,3-butylene glycol, glycerin, hexamethylene glycol, isoprene glycol, polyethylene glycol, hyaluronic acid, chondroitin sulfate, chitin, chitosan, xylitol, sorbitol, Maltitol, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO) PO adduct, Izayoi rose extract, yarrow extract Products, merryrot extract, dipropylene glycol and the like.

  In the composition for lips according to the present invention, one or more of the humectants may be selected and blended. The amount of water or humectant is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass in the composition. If the amount of water or humectant is too small, the moisturizing effect may be inferior, and if too much, the stability of the formulation may be poor.

  In the present invention, the lip composition is not particularly limited as long as it is a composition intended to be applied to the lips, such as lipstick and lip gloss, and is not limited to a stick, pencil or ointment. It can be used regardless of a specific form such as a liquid, gel or gel. The lip composition of the present invention can be produced, for example, by heating and melting a mixture containing the above essential components, pouring the mixture into a stick or an inner dish, and solidifying by cooling. Further, the lip composition of the present invention can be applied to lipsticks and lip glosses that are makeup cosmetics, as well as lip creams and the like that do not contain colorants.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
First, the structure of each monomer used in the production of the copolymer of the present invention is shown below.

Monomer A1:

Monomer A2:

Monomer B1:

Monomer C1:

Monomer C2:

Next, a method for synthesizing the copolymer used in the present invention will be described.
Copolymer 1-1
In a glass flask equipped with a stirrer, a thermometer, and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and polyoxymethacrylate represented by the above general formula (13) 5 parts by mass of ethylene ether (monomer B1), 60 parts by mass of methacryloxypropyl polydimethylsiloxane (monomer C1) represented by the general formula (14), 120 parts by mass of isopropanol, and dimethyl-2,2′-azobis (2- 4 parts by mass of methyl propionate) was added, heated under a nitrogen stream, and polymerized at 80 ° C. for 10 hours. Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 1-1.

The present inventors prepared various copolymers according to the synthesis method shown above, and performed the following evaluations.
Blending of copolymer The inventors first prepared various copolymers according to the above production example, blended a lipstick blended with the copolymer as a film-forming component, and a conventional film-forming component. A comparison was made with the lipstick. The monomer composition of the copolymer used in each test example, the blending composition of lipstick, and the evaluation results are also shown in Table 1 below. The evaluation criteria are as follows.

(1) Makeup The actual use test was conducted by 10 expert panelists on the presence or absence of lipstick makeup in each test example. Evaluation criteria are as follows: A: Eight or more panelists recognized that makeup was good.
○: 6 or more panelists and less than 8 panelists admitted that they had good makeup.
Δ: 3 or more panelists and less than 6 panelists recognized that makeup was good.
X: Less than 3 panelists recognized that makeup was good.

(2) Feeling of the coating With regard to the presence or absence of the coating feeling of the lipstick in each test example, an actual use test was conducted by 10 professional panelists. Evaluation criteria are as follows: A: Eight or more panelists recognized that there was no film feeling.
○: 6 or more panelists and less than 8 panelists recognized that there was no film feeling.
Δ: 3 or more and less than 6 panelists recognized that there was no film feeling.
X: Less than 3 panelists recognized that there was no film feeling.

(3) Luster With regard to the presence or absence of lipstick in each test example, an actual use test was conducted by 10 professional panelists. The evaluation criteria are as follows: A: Eight or more panelists recognized that the gloss was good.
○: 6 or more panelists and less than 8 panelists recognized that gloss was good.
Δ: 3 or more panelists and less than 6 panelists recognized that gloss was good.
X: Less than 3 panelists recognized that gloss was good.

(4) Solubility in formulation The solubility in the formulation of the copolymer was evaluated for the lipstick of each test example. The evaluation criteria are as follows.
A: The solubility was good.
X: Solubility was poor and could not be formulated.

From Table 1 above, the lipstick of Test Example 1-1 in which the copolymer 1-1 was blended as a film-forming component showed an extremely excellent effect of makeup retention and the film feeling was remarkably improved. It became clear.
On the other hand, in the case of Test Example 1-2 in which the copolymer 1-2 consisting only of the monomer A is blended, and Test Example 1-3 in which the copolymer 1-3 consisting of the monomer A and B is blended, Due to poor solubility in it, it could not be formulated. In addition, in the case of Test Example 1-4 in which the copolymer 1-4 composed of monomers A and C was blended, a film feeling was produced on the lips. Further, in Test Example 1-5 in which trimethylsiloxysilicic acid, which is known as a general film-forming component, was blended as a film-forming component, the makeup lasting, film feeling, and gloss were all inferior. In the blended Test Example 1-6, although the makeup durability, the coating feeling, and the gloss are improved, it is difficult to say that it is sufficient.

Following the monomer composition of the copolymer, the present inventors found that a copolymer To investigate the preferred monomer composition of the various copolymers obtained by changing the content of the monomer (A) according to the above Production Example The lipsticks prepared and blended with the respective copolymers were evaluated. Table 2 shows the composition and evaluation results of the lipstick of each test example. The evaluation criteria are the same as in the above test.

From Table 2 above, Test Example 1-7 using the copolymer 1-5 containing no monomer (A) is significantly inferior in terms of longevity. On the other hand, as the proportion of the monomer (A) in the copolymer increases, it can be seen that the makeup holding point tends to be improved, but the proportion of the monomer (A) is less than 20% by mass. In Test Examples 1-8 and 9 using the copolymers 1-6 and 7, it is difficult to say that they are sufficient in terms of long lasting makeup. On the other hand, in Test Examples 1-10 to 13 using the copolymers 1-8 to 11 in which the proportion of the monomer (A) in the copolymer is 20% by mass or more, both the makeup durability and the film feeling are extremely high. It turned out to be excellent.
From this, in the composition for lips according to the present invention, it is considered that the proportion of the monomer (A) in the copolymer needs to be 20% by mass or more.

Following copolymer concentration of lip compositions, the present inventors to consider the preferred formulation concentration of the copolymer to be blended into the lip compositions, the amount of the copolymer is varied is A lipstick was prepared and evaluated. Table 3 shows the composition of the lipstick and the evaluation results of each test example. The evaluation criteria are the same as in the above test.

  From Table 3 above, in Test Example 1-15 in which about 1% by mass of the copolymer 1-1 was blended, the effects of improving makeup, feeling of coating, and gloss can be seen. On the other hand, Test Example 1-19 containing about 30% by mass of copolymer 1-1 tends to be inferior in terms of film feeling. From this, it is thought that it is suitable to mix | blend 1-25 mass% of copolymers in the composition for lips concerning this invention.

Other examples of the present invention will be given below, but the present invention is not limited thereto.
Copolymer 2-1
In a glass flask equipped with a stirrer, a thermometer, and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and polyoxymethacrylate represented by the above general formula (13) 15 parts by mass of ethylene ether (monomer B1), 50 parts by mass of methacryloxypropyl polydimethylsiloxane (monomer C1) represented by the general formula (14), 120 parts by mass of isopropanol, and dimethyl-2,2′-azobis (2- 4 parts by mass of methyl propionate) was added, heated under a nitrogen stream, and polymerized at 80 ° C. for 10 hours. Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 2-1.

Copolymer 2-2
In a glass flask equipped with a stirrer, a thermometer and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and 2-acrylic acid represented by the above general formula (12) 15 parts by mass of ethylhexyl (monomer A2), 5 parts by mass of polyoxyethylene ether of methacrylic acid (monomer B1) represented by the above general formula (13), methacryloxypropyl polydimethylsiloxane represented by the above general formula (15) (monomer C2 ) 45 parts by mass, 120 parts by mass of isopropanol, and 4 parts by mass of dimethyl-2,2′-azobis (2-methylpropionate) were heated under a nitrogen stream, and a polymerization reaction was carried out at 80 ° C. for 10 hours. . Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 2-2.

Example 2-1
Lipstick mass%
Microcrystalline wax 1.0
Paraffin 11.0
Candelilla Row 3.0
Decamethylcyclopentasiloxane (in general formula (5), y = 5) balance dimethylpolysiloxane (in general formula (4), x = 2) 20.0
Alkyl-modified silicone 10.0
(In the general formula (6), R ⁹ = C ₈ H ₁₇ )
Copolymer 2-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 10.0
(In general formula (8), R ¹¹ = Ph, R ¹² = CH ₃ , R ¹³ = C ₈ F ₁₇ , b = 2, q = 2, r = 2, s = 3)
Alkoxy modified silicone 2.0
(In the general formula (9), R ¹⁴ = C ₁₈ H ₃₇ , t = 5, u = 3)
2-Ethylhexyl paramethoxycinnamate 1.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-1 was excellent in makeup, had no film feeling, and was excellent in gloss.

Example 2-2
Lipstick mass%
Microcrystalline wax 0.5
Candelilla Row 1.0
Synthetic wax (FNP-0090: Nippon Seiwa Co., Ltd.) 8.0
Decamethylcyclopentasiloxane remainder dimethylpolysiloxane (in formula (4), x = 2) 20.0
Alkyl-modified silicone 10.0
(In the general formula (6), R ⁹ = C ₈ H ₁₇ )
Copolymer 1-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 10.0
(In general formula (8), R ¹¹ = Ph, R ¹² = CH ₃ , R ¹³ = C ₈ F ₁₇ , b = 2, q = 2, r = 2, s = 3)
Alkoxy modified silicone 2.0
(In the general formula (9), R ¹⁴ = C ₁₈ H ₃₇ , t = 5, u = 3)
2-Ethylhexyl paramethoxycinnamate 1.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-2 was excellent in makeup, had no coating feeling, and was excellent in gloss.

Example 2-3
Lipstick mass%
Microcrystalline wax 2.0
Paraffin 1.0
Polyethylene wax (average molecular weight 500) 10.0
Carnavalou 1.0
Decamethylcyclopentasiloxane remainder dimethylpolysiloxane (in formula (4), x = 2) 30.0
Copolymer 2-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified dimethyl silicone 5.0
(In the general formula (7), R ¹⁰ = C ₈ F ₁₇ , a = 11, o = 11, p = 75)
Alkoxy modified silicone 2.0
(In the general formula (9), R ¹⁴ = C ₁₈ H ₃₇ , t = 5, u = 3)
Alkyl modified silicone 3.0
(In the general formula (10), R ¹⁵ = C ₁₈ H ₃₇ , v = 5, w = 3)
Tri (hydrogenated rosin / isostearic acid) glyceryl 5.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-3 was excellent in makeup, had no coating feeling, and was excellent in gloss.

Example 2-4
Emulsified lipstick mass%
Microcrystalline wax 1.0
Paraffin 12.0
Candelilla Row 2.0
Decamethylcyclopentasiloxane Remainder Copolymer 2-2 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Tri (hydrogenated rosin / isostearic acid) glyceryl 5.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume proper amount Laponite 0.4
Glycerin 0.5
Water 0.1
(Manufacturing method) Components other than aqueous phase parts (laponite, glycerin, water) are mixed and dissolved at 95 ° C, and after adding and emulsifying the aqueous phase parts with stirring, the mixture is poured into a container and cooled and solidified to emulsify lipstick. Got.
The lipstick of Example 2-4 was excellent in makeup, had no coating feeling, and was excellent in gloss.

Example 2-4
Liquid lipstick mass%
Microcrystalline wax 0.2
Paraffin 2.0
Decamethylcyclopentasiloxane Residual copolymer 2-2 15.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 20.0
(In the general formula (8), R ¹¹ = Ph, R ¹² = CH ₃ ,
R ¹³ = C ₈ F ₁₇ , b = 3, q = 6, r = 20, s = 100)
Silica (Aerosil R972: Degussa) 2.0
Pigment 5.0
Perfume proper amount Laponite 0.4
Glycerin 0.5
Water 0.1
(Manufacturing method) Components other than aqueous phase parts (laponite, glycerin, water) are mixed and dissolved at 95 ° C, and after adding and emulsifying the aqueous phase parts with stirring, the mixture is poured into a container and cooled and solidified to emulsify lipstick. Got.
The lipstick of Example 2-5 was excellent in makeup, had no coating feeling, and was excellent in gloss.

Claims (4)

It contains a monomer (A) represented by the following general formula (1), a monomer (B) represented by the following general formula (2), and a monomer (C) represented by the following general formula (3) as constituent monomers. A composition for lips, containing a copolymer polymer in which the content of the monomer (A) is 20% by mass or more based on the total amount of the constituent monomers.

(In the above formula, R ¹ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, and R ² represents hydrogen or a hydrocarbon group having 1 to 24 carbon atoms.)

(In the above formula, R ³ is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁴ is a divalent hydrocarbon group having 1 to ⁴ carbon atoms, R ⁵ is hydrogen or a hydrocarbon having 1 to 24 carbon atoms. Represents a group, and l represents an integer of 1 to 50.)

(In the above formula, R ⁶ represents hydrogen or a hydrocarbon group having 1 to 3 carbon atoms, R ⁷ represents a divalent hydrocarbon group having 1 to 4 carbon atoms, and R ⁸ represents a hydrocarbon group having 1 to 6 carbon atoms. M represents 0 to 500, and n represents an integer of 1 to 3.) The composition for lips according to claim 1, further comprising a linear silicone oil represented by the following general formula (4), a cyclic silicone oil represented by the following general formula (5), and an alkyl represented by the following general formula (6). A lip composition comprising one or more volatile oils selected from a modified silicone oil and isoparaffin.

(In the above formula, x represents an integer of 0 to 3.)

(In the above formula, y represents an integer of 3 to 6.)

(In the above formula, ^{R 9} represents a hydrocarbon group having 2 to 8 carbon atoms.) The lip composition according to claim 1 or 2, further comprising a fluorine-modified dimethyl silicone represented by the following general formula (7), a fluorine-modified phenyl silicone represented by the following general formula (8), and the following general formula (9): 1 or 2 or more types selected from the alkoxy-modified silicone shown, the alkyl-modified silicone shown by the following general formula (10), tri (hydrogenated rosin / isostearic acid) glyceryl, and 2-ethylhexyl paramethoxycinnamate The composition for lips characterized by containing the non-volatile oil component.

(Wherein, o and p are average numbers, o is an integer of 1 to 150, p is an integer of 0 to 150, the sum of o and p is 4 or more, a is an integer of 0 to ¹⁰ , and R ¹⁰ is Represents a perfluoroalkyl group having 1 to 12 carbon atoms.)

(In the formula, q, r, and s are average numbers, q is 1 to 150, r is 1 to 150, s is an integer of 0 to 150, and the sum of q, r, and s is 4 or more, b 0-10 ^integers, R ^{11, R 12} represents a methyl group or a phenyl ^group, at least one of the phenyl groups of R ^{11, R 12, R 13} is a perfluoroalkyl group having 1 to 12 carbon atoms Represents.)

(In the formula, OR ¹⁴ represents an alkoxy group having 2 to 30 carbon atoms, t and u are average numbers, t represents 1 to 500, u represents an integer of 0 to 500, and the sum of t and u is 4 or more. is there.)

(In the formula, R ¹⁵ represents an alkyl group having 10 to 30 carbon atoms, v and w are average numbers, v represents 1 to 500, w represents an integer of 0 to 500, and the sum of v and w is 4 or more. is there.) The lip composition according to any one of claims 1 to 3, further comprising water and / or a humectant.