JP2014009189A5 - - Google Patents
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- JP2014009189A5 JP2014009189A5 JP2012146191A JP2012146191A JP2014009189A5 JP 2014009189 A5 JP2014009189 A5 JP 2014009189A5 JP 2012146191 A JP2012146191 A JP 2012146191A JP 2012146191 A JP2012146191 A JP 2012146191A JP 2014009189 A5 JP2014009189 A5 JP 2014009189A5
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- 125000004432 carbon atoms Chemical group C* 0.000 claims description 37
- 239000000178 monomer Substances 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 23
- 210000003491 Skin Anatomy 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000002209 hydrophobic Effects 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 10
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-Threitol Natural products OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N 3-(2,3-dihydroxypropoxy)propane-1,2-diol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- 229940105990 DIGLYCERIN Drugs 0.000 claims description 2
- 239000004386 Erythritol Substances 0.000 claims description 2
- 229940009714 Erythritol Drugs 0.000 claims description 2
- UNXHWFMMPAWVPI-IMJSIDKUSA-N L-threitol Chemical compound OC[C@H](O)[C@@H](O)CO UNXHWFMMPAWVPI-IMJSIDKUSA-N 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N Trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004429 atoms Chemical group 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 229960001735 pentaerythritol Drugs 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims 2
- 230000003020 moisturizing Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- -1 acrylic ester Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 230000000379 polymerizing Effects 0.000 description 1
Description
このような状況に鑑み、本発明者等は、優れた保湿効果と、べたつき及びきしみのない優れた使用感を有する皮膚外用剤を求めて鋭意研究した結果、一つの（メタ）アクロイル基及び複数の、特定の分岐構造のアシル基を有するアクリルエステル系モノマーと、特定の親水性構造のアクリル系モノマーを重合して得られるコポリマーが皮膚外用剤に高い保湿効果とべたつき及びきしみのない優れた使用感を与えることを見出し、本発明に至った。すなわち、本発明は以下の通りである。
（１）下記一般式（Ｉ）または（ＩＩ）で表される疎水性モノマーから誘導される一種または二種以上の構成単位と下記Ａ群からなる親水性モノマーから誘導される一種または二種以上の構成単位を必須構成単位として有し、他の構成単位を有していてもよいコポリマーを含有することを特徴とする皮膚外用剤。
一般式（Ｉ）
（一般式（Ｉ）中Ｒ１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ２，Ｒ３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｐは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（ＩＩ）
（一般式（ＩＩ）中Ｒ４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ５，Ｒ６，Ｒ７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｑは四価のアルコールからＯＨ基が脱離した基を表す。）
Ａ群：重合性カルボン酸、下記一般式（ＩＩＩ）で表される親水性モノマー
一般式（ＩＩＩ）
（一般式（ＩＩＩ）中Ｒ8は水素原子または炭素数１〜３のアルキル基を表し、Ｒ9は水酸基を有していてもよい炭素数２〜４のアルキレン基を表し、Ｒ10は水素原子、炭素数６〜１０の芳香族炭化水素基、炭素数１〜１４の脂肪族炭化水素基又は炭素数１〜１２のアシル基を表す。ｎは６〜４０の整数を表す。）（２）一般式（Ｉ）で表される疎水性モノマーが下記一般式（ＩＶ）で表される疎水性モノマーであり、かつ、一般式（ＩＩ）で表される疎水性モノマーが下記一般式（Ｖ）で表される疎水性モノマーであることを特徴とする（１）記載の皮膚外用剤。
一般式（ＩＶ）
（一般式（ＩＶ）中Ｒ１１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１２，Ｒ１３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｓは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（Ｖ）
（一般式（Ｖ）中Ｒ１４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１５，Ｒ１６，Ｒ１７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｔは四価のアルコールからＯＨ基が脱離した基を表す。）
（３）一般式（ＩＩＩ）で表される親水性モノマーが、下記一般式（ＶＩ）で表される親水性モノマーであることを特徴とする（１）または（２）記載の皮膚外用剤。
一般式（ＶＩ）
（一般式（ＶＩ）中Ｒ１８は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１９は水素原子、炭素数６〜１０の芳香族炭化水素基、炭素数１〜１４の脂肪族炭化水素基又は炭素数１〜１２のアシル基を表す。ｍは６〜４０の整数を表す。）
（４）重合性カルボン酸がアクリル酸及び／またはメタクリル酸であることを特徴とする（１）〜（３）いずれかに記載の皮膚外用剤。
（５）三価アルコールがグリセリン、トリメチロールプロパン、トリメチロールエタンからなる群から選択されることを特徴とする（１）〜（４）いずれかに記載の皮膚外用剤。
（６）四価のアルコールがジグリセリン、ペンタエリスリトール、エリスリトール、Ｄ−トレイトール、Ｌ−トレイトールからなる群から選択される四価のアルコールであることを特徴とする（１）〜（４）いずれかに記載の皮膚外用剤。
（７）疎水性モノマーから誘導される一種または二種以上の構成単位がコポリマーの全構成単位の１〜４０質量％である、かつ、親水性モノマーから誘導される一種または二種以上の構成単位がコポリマーの全構成単位の３０〜９５質量％であることを特徴とする、（１）〜（６）いずれかに記載の皮膚外用剤。
（８）化粧料であることを特徴とする（１）〜（７）の何れかに記載の皮膚外用剤。
In view of such a situation, the present inventors have intensively studied for an external preparation for skin having an excellent moisturizing effect and an excellent feeling of use without stickiness and creaking. As a result, one (meth) acryloyl group and plural The use of an acrylic ester monomer having an acyl group having a specific branched structure and a copolymer obtained by polymerizing an acrylic monomer having a specific hydrophilic structure has a high moisturizing effect and excellent use without stickiness and creaking. It found out that it gave a feeling and came to this invention. That is, the present invention is as follows.
(1) One or two or more structural units derived from a hydrophobic monomer represented by the following general formula (I) or (II) and one or more structural units derived from a hydrophilic monomer consisting of the following group A The skin external preparation characterized by containing the copolymer which may have other structural units as an essential structural unit.
Formula (I)
(In the general formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 may be the same or different, have no ring structure and have a branched carbon number. Represents an acyl group of 6 to 22. P represents a group in which an OH group is eliminated from a trivalent alcohol.
Formula (II)
(In the general formula (II), R 4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 5 , R 6 and R 7 may be the same or different and do not contain a ring structure and have a branch. Represents an acyl group having 6 to 22 carbon atoms, Q represents a group in which an OH group is eliminated from a tetravalent alcohol.
Group A: polymerizable carboxylic acid, hydrophilic monomer represented by the following general formula (III) general formula (III)
(In general formula (III), R 8 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 9 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R 10 represents hydrogen. An atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aliphatic hydrocarbon group having 1 to 14 carbon atoms, or an acyl group having 1 to 12 carbon atoms, n represents an integer of 6 to 40) (2 ) The hydrophobic monomer represented by the general formula (I) is a hydrophobic monomer represented by the following general formula (IV), and the hydrophobic monomer represented by the general formula (II) is represented by the following general formula (V The skin external preparation according to (1), which is a hydrophobic monomer represented by
Formula (IV)
(In the general formula (IV), R 11 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 12 and R 13 may be the same or different, have no ring structure, and have a branched carbon number. It represents an acyl group having 10 to 22 or a C 6-9 acyl group having two or more branches that does not contain a ring structure, and S represents a group in which an OH group is eliminated from a trivalent alcohol. )
General formula (V)
(In the general formula (V), R 14 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 15 , R 16 , and R 17 may be the same or different and do not include a ring structure and have a branch. Represents an acyl group having 10 to 22 carbon atoms, or an acyl group having 6 to 9 carbon atoms having two or more branches that does not contain a ring structure, and T represents a group in which an OH group is eliminated from a tetravalent alcohol. Represents.)
(3) The skin external preparation according to (1) or (2), wherein the hydrophilic monomer represented by the general formula (III) is a hydrophilic monomer represented by the following general formula (VI).
Formula (VI)
(In the general formula (VI), R 18 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 19 represents a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aliphatic group having 1 to 14 carbon atoms. A hydrocarbon group or a C1-C12 acyl group is represented.m represents an integer of 6-40.)
(4) The external preparation for skin according to any one of (1) to (3), wherein the polymerizable carboxylic acid is acrylic acid and / or methacrylic acid.
(5) The external preparation for skin according to any one of (1) to (4), wherein the trihydric alcohol is selected from the group consisting of glycerin, trimethylolpropane, and trimethylolethane.
(6) The tetravalent alcohol is a tetravalent alcohol selected from the group consisting of diglycerin, pentaerythritol, erythritol, D-threitol, and L-threitol (1) to (4) The external preparation for skin according to any one of the above.
(7) One or two or more structural units derived from a hydrophobic monomer is 1 to 40% by mass of the total structural units of the copolymer, and one or two or more structural units derived from a hydrophilic monomer The external preparation for skin according to any one of (1) to (6), characterized in that is 30 to 95% by mass of the total structural unit of the copolymer.
(8) The external preparation for skin according to any one of (1) to (7), which is a cosmetic.
以下、本発明を詳細に説明する。
＜１＞ 本発明の皮膚外用剤の必須成分であるコポリマーを構成する疎水性モノマーから誘導される構成単位。
本発明の皮膚外用剤の必須成分であるコポリマー（以下、単に本発明のコポリマーと呼ぶ場合がある）は下記一般式（Ｉ）又は一般式（ＩＩ）で表される疎水性モノマーから誘導される構成単位（以下、単に、「構成単位Ｉ」または「構成単位ＩＩ」と呼ぶこともある）の一種または二種以上を必須構成単位として含有する。
一般式（Ｉ）
（一般式（Ｉ）中Ｒ１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ２，Ｒ３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｐは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（ＩＩ）
（一般式（ＩＩ）中Ｒ４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ５，Ｒ６，Ｒ７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｑは四価のアルコールからＯＨ基が脱離した基を表す。）
Hereinafter, the present invention will be described in detail.
<1> A structural unit derived from a hydrophobic monomer constituting a copolymer which is an essential component of the external preparation for skin of the present invention.
The copolymer which is an essential component of the external preparation for skin of the present invention (hereinafter sometimes simply referred to as the copolymer of the present invention) is derived from a hydrophobic monomer represented by the following general formula (I) or general formula (II) One type or two or more types of structural units (hereinafter sometimes simply referred to as “structural unit I” or “structural unit II”) are contained as essential structural units.
Formula (I)
(In the general formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 may be the same or different, have no ring structure and have a branched carbon number. Represents an acyl group of 6 to 22. P represents a group in which an OH group is eliminated from a trivalent alcohol.
Formula (II)
(In the general formula (II), R 4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 5 , R 6 and R 7 may be the same or different and do not contain a ring structure and have a branch. Represents an acyl group having 6 to 22 carbon atoms, Q represents a group in which an OH group is eliminated from a tetravalent alcohol.
上記一般式（Ｉ）又は（ＩＩ）で表される疎水性モノマーの中でも特に好ましいものとして、下記一般式（ＩＶ）又は（Ｖ）で表される疎水性モノマーが挙げられる。
一般式（ＩＶ）
（一般式（ＩＶ）中Ｒ１１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１２，Ｒ１３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｓは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（Ｖ）
（一般式（Ｖ）中Ｒ１４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１５，Ｒ１６，Ｒ１７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｔは四価のアルコールからＯＨ基が脱離した基を表す。）
Among the hydrophobic monomers represented by the general formula (I) or (II), a hydrophobic monomer represented by the following general formula (IV) or (V) is particularly preferable.
Formula (IV)
(In the general formula (IV), R 11 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 12 and R 13 may be the same or different, have no ring structure, and have a branched carbon number. It represents an acyl group having 10 to 22 or a C 6-9 acyl group having two or more branches that does not contain a ring structure, and S represents a group in which an OH group is eliminated from a trivalent alcohol. )
General formula (V)
(In the general formula (V), R 14 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 15 , R 16 , and R 17 may be the same or different and do not include a ring structure and have a branch. Represents an acyl group having 10 to 22 carbon atoms, or an acyl group having 6 to 9 carbon atoms having two or more branches that does not contain a ring structure, and T represents a group in which an OH group is eliminated from a tetravalent alcohol. Represents.)
Claims (8)
一般式（Ｉ）
（一般式（Ｉ）中Ｒ１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ２，Ｒ３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｐは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（ＩＩ）
（一般式（ＩＩ）中Ｒ４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ５，Ｒ６，Ｒ７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数６〜２２のアシル基を表す。Ｑは四価のアルコールからＯＨ基が脱離した基を表す。）
Ａ群：重合性カルボン酸、下記一般式（ＩＩＩ）で表される親水性モノマー
一般式（ＩＩＩ）
（一般式（ＩＩＩ）中Ｒ8は水素原子または炭素数１〜３のアルキル基を表し、Ｒ9は水酸基を有していてもよい炭素数２〜４のアルキレン基を表し、Ｒ10は水素原子、炭素数６〜１０の芳香族炭化水素基、炭素数１〜１４の脂肪族炭化水素基又は炭素数１〜１２のアシル基を表す。ｎは６〜４０の整数を表す。） One or more structural units derived from a hydrophobic monomer represented by the following general formula (I) or (II) and one or more structural units derived from a hydrophilic monomer consisting of the following group A A skin external preparation characterized by containing a copolymer which has an essential constituent unit and may have other constituent units.
Formula (I)
(In the general formula (I), R 1 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 may be the same or different, have no ring structure and have a branched carbon number. Represents an acyl group of 6 to 22. P represents a group in which an OH group is eliminated from a trivalent alcohol.
Formula (II)
(In the general formula (II), R 4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 5 , R 6 and R 7 may be the same or different and do not contain a ring structure and have a branch. Represents an acyl group having 6 to 22 carbon atoms, Q represents a group in which an OH group is eliminated from a tetravalent alcohol.
Group A: polymerizable carboxylic acid, hydrophilic monomer represented by the following general formula (III) general formula (III)
(In general formula (III), R 8 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 9 represents an alkylene group having 2 to 4 carbon atoms which may have a hydroxyl group, and R 10 represents hydrogen. An atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms, an aliphatic hydrocarbon group having 1 to 14 carbon atoms, or an acyl group having 1 to 12 carbon atoms, and n represents an integer of 6 to 40.)
一般式（ＩＶ）
（一般式（ＩＶ）中Ｒ１１は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１２，Ｒ１３は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｓは三価のアルコールからＯＨ基が脱離した基を表す。）
一般式（Ｖ）
（一般式（Ｖ）中Ｒ１４は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１５，Ｒ１６，Ｒ１７は同一でも異なっていてもよく、環構造を含まない、分岐を有する、炭素数１０〜２２のアシル基、または、環構造を含まない、２つ以上の分岐を有する炭素数６〜９のアシル基を表す。Ｔは四価のアルコールからＯＨ基が脱離した基を表す。） The hydrophobic monomer represented by the general formula (I) is a hydrophobic monomer represented by the following general formula (IV), and the hydrophobic monomer represented by the general formula (II) is represented by the following general formula (V) The external preparation for skin according to claim 1, which is a hydrophobic monomer represented by the formula:
Formula (IV)
(In the general formula (IV), R 11 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 12 and R 13 may be the same or different, have no ring structure, and have a branched carbon number. It represents an acyl group having 10 to 22 or a C 6-9 acyl group having two or more branches that does not contain a ring structure, and S represents a group in which an OH group is eliminated from a trivalent alcohol. )
General formula (V)
(In the general formula (V), R 14 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R 15 , R 16 , and R 17 may be the same or different and do not include a ring structure and have a branch. Represents an acyl group having 10 to 22 carbon atoms, or an acyl group having 6 to 9 carbon atoms having two or more branches that does not contain a ring structure, and T represents a group in which an OH group is eliminated from a tetravalent alcohol. Represents.)
一般式（ＶＩ）
（一般式（ＶＩ）中Ｒ１８は水素原子または炭素数１〜３のアルキル基を表し、Ｒ１９は水素原子、炭素数６〜１０の芳香族炭化水素基、炭素数１〜１４の脂肪族炭化水素基又は炭素数１〜１２のアシル基を表す。ｍは６〜４０の整数を表す。） The skin external preparation according to claim 1 or 2, wherein the hydrophilic monomer represented by the general formula (III) is a hydrophilic monomer represented by the following general formula (VI).
Formula (VI)
(In the general formula (VI), R 18 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R 19 represents a hydrogen atom, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aliphatic group having 1 to 14 carbon atoms. A hydrocarbon group or a C1-C12 acyl group is represented.m represents an integer of 6-40.)
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| JP2012146191A JP6144466B2 (en) | 2012-06-29 | 2012-06-29 | Topical skin preparation |
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| JP2014009189A JP2014009189A (en) | 2014-01-20 |
| JP2014009189A5 true JP2014009189A5 (en) | 2015-07-23 |
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| JP2016056153A (en) * | 2014-09-12 | 2016-04-21 | 大阪有機化学工業株式会社 | Cyclic acetal (meth)acrylate composition |
| JP6584141B2 (en) * | 2015-05-26 | 2019-10-02 | ポーラ化成工業株式会社 | Sunscreen cosmetics |
| JP6608622B2 (en) * | 2015-06-04 | 2019-11-20 | ポーラ化成工業株式会社 | Emulsified composition |
| JP6608612B2 (en) * | 2015-05-11 | 2019-11-20 | ポーラ化成工業株式会社 | Copolymer |
| JP6618713B2 (en) * | 2015-05-26 | 2019-12-11 | ポーラ化成工業株式会社 | Skin cleanser |
| CN111329788B (en) * | 2015-05-11 | 2023-03-31 | 宝丽化学工业有限公司 | Copolymer |
| JP6815719B2 (en) * | 2015-05-11 | 2021-01-20 | ポーラ化成工業株式会社 | A film having a sea-island structure and a composition forming the film |
| JP6968628B2 (en) * | 2017-09-04 | 2021-11-17 | ポーラ化成工業株式会社 | Emulsifying composition |
| WO2024018286A2 (en) * | 2022-07-17 | 2024-01-25 | The Hong Kong University Of Science And Technology | Compositions of lipophilic anchors and the use thereof |
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| JP6042118B2 (en) * | 2012-06-29 | 2016-12-14 | ポーラ化成工業株式会社 | New esters of trihydric alcohols |
| JP5944244B2 (en) * | 2012-06-29 | 2016-07-05 | ポーラ化成工業株式会社 | New copolymer |
| JP6004784B2 (en) * | 2012-06-29 | 2016-10-12 | ポーラ化成工業株式会社 | New tetrahydric alcohol esters |
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