JPH051081A - Phosphoric acid ester and/or its salt and production thereof - Google Patents
Phosphoric acid ester and/or its salt and production thereofInfo
- Publication number
- JPH051081A JPH051081A JP14750591A JP14750591A JPH051081A JP H051081 A JPH051081 A JP H051081A JP 14750591 A JP14750591 A JP 14750591A JP 14750591 A JP14750591 A JP 14750591A JP H051081 A JPH051081 A JP H051081A
- Authority
- JP
- Japan
- Prior art keywords
- phosphoric acid
- salt
- acid ester
- polyglycerol
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Cosmetics (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は香化粧品用基剤、コンデ
ィショニング剤、保湿剤、キレート剤や表面改質剤等と
して有用な新規リン酸エステル又はその塩、及びその製
造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel phosphoric acid ester or a salt thereof useful as a base for perfumed cosmetics, a conditioning agent, a moisturizing agent, a chelating agent, a surface modifier, etc., and a method for producing the same.
【０００２】[0002]
【従来の技術】従来、脂肪酸やアルキルリン酸のアルミ
ニウム塩、亜鉛塩、チタン塩等の有機酸塩は、ファンデ
ーション用粉体、白粉、サンスクリーン剤等として化粧
品中に広く配合されている。2. Description of the Related Art Conventionally, organic acid salts such as aluminum salts, zinc salts and titanium salts of fatty acids and alkylphosphoric acids have been widely blended in cosmetics as powders for foundations, white powders, sunscreen agents and the like.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、これら
の有機酸塩は水や有機溶媒に対する溶解度が極めて低い
ため、これを配合した化粧品等の使用形態が粉体やサス
ペンジョン等に限定されるという欠点があった。このた
め、水や有機溶媒と混合したとき均一な溶液となり、種
々の形態での使用が可能な有機酸塩が望まれていた。However, since these organic acid salts have extremely low solubilities in water and organic solvents, the use form of cosmetics and the like containing them is limited to powders and suspensions. there were. Therefore, an organic acid salt that can be used in various forms has been desired, which is a uniform solution when mixed with water or an organic solvent.
【０００４】[0004]
【課題を解決するための手段】かかる実情において、本
発明者は数多くのリン酸エステル及びその塩を合成し、
その性質について検討をしてきたところ、縮合度２以上
のポリグリセリンのリン酸エステルの塩が水と混合した
とき均一な溶液となり、広範囲の香化粧品等に配合でき
るものであることを見出し、本発明を完成した。In such a situation, the present inventor has synthesized a number of phosphoric acid esters and salts thereof,
As a result of studying its properties, it was found that when a salt of phosphoric acid ester of polyglycerin having a degree of condensation of 2 or more becomes a uniform solution when mixed with water, it can be blended in a wide range of fragrance cosmetics, etc. Was completed.
【０００５】すなわち、本発明は次の一般式（１）That is, the present invention has the following general formula (1):
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】で表わされるリン酸エステル又はその塩、
及びその製造方法を提供するものである。A phosphoric acid ester represented by or a salt thereof,
And a method for manufacturing the same.
【０００８】一般式（１）において、Ｚを構成する縮合
度２以上のポリグリセリンの縮合度は、特に制限されな
いが、２〜１００、特に２〜１０が好ましい。本発明に
おいて、縮合度２のポリグリセリンとは、ジグリセリン
を意味する。また、ｎは１以上でポリグリセリンの水酸
基数までの範囲であれば特に制限されないが、ｎ＝１〜
２が特に好ましい。また、リン酸エステル（１）の塩と
しては、ナトリウム塩、カリウム塩、マグネシウム塩、
カルシウム塩、鉄塩、亜鉛塩、チタン塩、アルミニウム
塩などの金属塩；アンモニウム塩などのオニウム塩；ト
リエタノールアミン塩、ジエタノールアミン塩、アルキ
ルアミン塩などのアミン塩等が挙げられる。In the general formula (1), the degree of condensation of polyglycerin having a degree of condensation of 2 or more and which constitutes Z is not particularly limited, but is preferably 2 to 100, particularly preferably 2 to 10. In the present invention, polyglycerin having a condensation degree of 2 means diglycerin. Further, n is not particularly limited as long as it is in the range of 1 or more and the number of hydroxyl groups of polyglycerin, but n = 1 to 1
2 is particularly preferred. The salts of phosphoric acid ester (1) include sodium salt, potassium salt, magnesium salt,
Examples thereof include metal salts such as calcium salts, iron salts, zinc salts, titanium salts and aluminum salts; onium salts such as ammonium salts; amine salts such as triethanolamine salts, diethanolamine salts and alkylamine salts.
【０００９】本発明のリン酸エステル（１）又はその塩
は、例えば縮合度２以上のポリグリセリンにリン酸化剤
を反応させることにより製造される。The phosphoric acid ester (1) or a salt thereof of the present invention is produced, for example, by reacting a polyglycerin having a condensation degree of 2 or more with a phosphorylating agent.
【００１０】本反応に使用されるリン酸化剤としては、
ポリリン酸；オキシ塩化リン等のオキシハロゲン化リ
ン；オルトリン酸、五酸化リン等が挙げられる。As the phosphorylating agent used in this reaction,
Examples thereof include polyphosphoric acid; phosphorus oxyhalides such as phosphorus oxychloride; orthophosphoric acid, phosphorus pentoxide and the like.
【００１１】本反応の条件は用いるリン酸化剤によって
異なり、オキシハロゲン化リンを用いる場合は例えば特
公昭５０−８０５２３号公報に、オルトリン酸や五酸化
リンを用いる場合は例えば特公昭４１−１４４１６号公
報に、ポリリン酸を用いる場合は例えば特公昭４３−２
６４９２号公報にそれぞれ記載の条件に従えばよい。The conditions of this reaction differ depending on the phosphorylating agent used. For example, when phosphorus oxyhalide is used, it is described in, for example, JP-B-50-80523, and when orthophosphoric acid or phosphorus pentoxide is used, it is, for example, JP-B-41-14416. When polyphosphoric acid is used in the publication, for example, Japanese Patent Publication No. 43-2
The conditions described in Japanese Patent No. 6492 may be followed.
【００１２】このようにして得られた反応混合物は、用
途によってはそのままで使用することもできるが、所望
ならば常法によりリン酸エステル（１）を単離して使用
することもできる。The reaction mixture thus obtained can be used as it is, depending on the intended use, or if desired, the phosphoric acid ester (1) can be isolated and used by a conventional method.
【００１３】さらにリン酸エステル（１）の塩は、リン
酸エステル（１）を対応する塩基、例えば水酸化ナトリ
ウム、水酸化カリウムなどの金属水酸化物、又はアルキ
ルアミン、アルカノールアミンなどのアミンで中和する
ことにより得られる。また、このようにして得られたリ
ン酸エステル（１）のアルカリ金属塩やアンモニウム塩
などと、亜鉛、アルミニウム、チタンなど遷移金属の水
溶性塩を、水性媒体中で反応させることにより、リン酸
エステル（１）の遷移金属塩を得ることができる。Further, the salt of phosphoric acid ester (1) is obtained by using phosphoric acid ester (1) with a corresponding base, for example, a metal hydroxide such as sodium hydroxide or potassium hydroxide, or an amine such as alkylamine or alkanolamine. Obtained by neutralizing. Further, by reacting the alkali metal salt or ammonium salt of the phosphoric acid ester (1) thus obtained with a water-soluble salt of a transition metal such as zinc, aluminum or titanium in an aqueous medium, phosphoric acid A transition metal salt of ester (1) can be obtained.
【００１４】本発明のリン酸エステル（１）の塩は水に
対する溶解性が良好であり、水溶液として、又は必要に
応じてエタノール、イソプロパノール、アセトン等を含
む溶液として使用することができる。さらに、水を除去
した粉体として使用することもできる。また目的に応じ
て、その他の成分と混合して使用することもでき、広い
範囲の形態での使用が可能である。The salt of the phosphoric acid ester (1) of the present invention has good solubility in water and can be used as an aqueous solution or, if necessary, as a solution containing ethanol, isopropanol, acetone or the like. Further, it can be used as a powder without water. Further, it can be used by mixing with other components depending on the purpose, and can be used in a wide range of forms.
【００１５】[0015]
【発明の効果】本発明のポリグリセリンリン酸エステル
（１）及びその塩は、水と混合すると均一な溶液を与
え、種々の形態での使用が可能であり、皮膚や毛髪に対
して優れたコンディショニング効果を示し、シャンプ
ー、リンス、化粧品等に配合することができる。INDUSTRIAL APPLICABILITY The polyglycerin phosphoric acid ester (1) and its salt of the present invention give a uniform solution when mixed with water and can be used in various forms, and are excellent for skin and hair. It has a conditioning effect and can be added to shampoos, rinses, cosmetics and the like.
【００１６】[0016]
【実施例】以下に実施例を挙げ、本発明をさらに詳細に
説明するが、本発明はこれらの実施例に限定されるもの
ではない。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００１７】実施例１
反応器にポリリン酸（１０５％リン酸）１７５ｇを入
れ、これにポリグリセリン（平均縮合度６）８７ｇを約
２時間かけて滴下し、その後８０℃まで徐々に昇温し、
８０℃で２４時間反応させた。反応後、反応物に水３０
ｇを加え、８０℃で約４時間処理した。この後、室温ま
で冷却後、水１８０ｇとMgCl2・6H2O １９０ｇを加え、
さらに２８％アンモニア水で反応混合物のpHを８に調整
し、生じた不溶物を濾過により除去した。得られた反応
物溶液をイオン交換樹脂（ダウエックス50WX8H+型）で
処理し、ポリグリセリン酸エステルの水溶液を得た。こ
れより凍結乾燥により溶媒を除去し、ポリグリセリン
（平均縮合度６）リン酸エステル３１ｇを得た（単離収
率３３％）。
リン酸含量；5.9 ％（計算値 5.7％；モノリン酸エステ
ルとして）Example 1 175 g of polyphosphoric acid (105% phosphoric acid) was placed in a reactor, 87 g of polyglycerin (average degree of condensation 6) was added dropwise thereto over about 2 hours, and then the temperature was gradually raised to 80 ° C. ,
The reaction was carried out at 80 ° C for 24 hours. After the reaction, water is added to the reaction product.
g, and treated at 80 ° C. for about 4 hours. After that, after cooling to room temperature, 180 g of water and 190 g of MgCl 2 .6H 2 O were added,
The pH of the reaction mixture was adjusted to 8 with 28% aqueous ammonia, and the resulting insoluble matter was removed by filtration. The resulting reaction solution was treated with an ion exchange resin (Dowex 50WX8H + type) to obtain an aqueous solution of polyglyceric acid ester. From this, the solvent was removed by freeze-drying to obtain 31 g of polyglycerin (average degree of condensation 6) phosphate ester (isolation yield 33%). Phosphoric acid content; 5.9% (calculated value 5.7%; as monophosphate ester)
【００１８】実施例２
実施例１で得られたポリグリセリン（平均縮合度６）リ
ン酸エステル１０ｇを５０ｇの水に溶解し、これに１Ｎ
水酸化ナトリウム水溶液３６ｇを加えた。得られたポリ
グリセリンリン酸エステルジナトリウム塩水溶液から凍
結乾燥により、ポリグリセリン（平均縮合度６）のリン
酸エステルジナトリウム塩１１ｇを得た。
リン含量5.5％ （計算値 5.3％；モノリン酸エス
テルとして）
ナトリウム含量7.9％（計算値 7.8％；モノリン酸エス
テルとして）Example 2 10 g of the polyglycerin (average degree of condensation 6) phosphoric acid ester obtained in Example 1 was dissolved in 50 g of water, and 1N was added thereto.
36 g of sodium hydroxide aqueous solution was added. By freeze-drying the obtained polyglycerin phosphate disodium salt aqueous solution, 11 g of phosphoric acid disodium salt of polyglycerin (average degree of condensation 6) was obtained. Phosphorus content 5.5% (calculated value 5.3%; as monophosphate ester) Sodium content 7.9% (calculated value 7.8%; as monophosphate ester)
【００１９】実施例３
実施例１で得られたポリグリセリン（平均縮合度６）リ
ン酸エステル１０ｇを５０ｇの水に溶解し、これに水酸
化亜鉛1.8gを粉末のまま加え、よく攪拌して溶解した。
得られたポリグリセリンリン酸エステル亜鉛塩水溶液か
ら凍結乾燥により、ポリグリセリン（平均縮合度６）の
リン酸エステル亜鉛塩１１ｇを得た。
リン含量5.2％ （計算値 5.1％；モノリン酸エス
テルとして）
亜鉛含量11.0％ （計算値 10.8％；モノリン酸エ
ステルとして）Example 3 10 g of the polyglycerin (average degree of condensation 6) phosphoric acid ester obtained in Example 1 was dissolved in 50 g of water, and 1.8 g of zinc hydroxide was added as a powder to this, and well stirred. Dissolved.
By freeze-drying the obtained polyglycerin phosphoric acid ester zinc salt aqueous solution, 11 g of phosphoric acid ester zinc salt of polyglycerin (average degree of condensation 6) was obtained. Phosphorus content 5.2% (calculated value 5.1%; as monophosphate ester) Zinc content 11.0% (calculated value 10.8%; as monophosphate ester)
─────────────────────────────────────────────────────
─────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成３年７月１９日[Submission date] July 19, 1991
【手続補正１】[Procedure Amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】請求項１[Name of item to be corrected] Claim 1
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【化１】 で表わされるリン酸エステル又はその塩。[Chemical 1] The phosphoric acid ester represented by or its salt.
【手続補正２】[Procedure Amendment 2]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００６[Correction target item name] 0006
【補正方法】変更[Correction method] Change
【補正内容】[Correction content]
【０００６】[0006]
【化２】 [Chemical 2]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 7/42 7252−4Ｃ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location A61K 7/42 7252-4C
Claims (3)
化剤を反応させることを特徴とする請求項１記載のリン
酸エステル又はその塩の製造方法。2. The method for producing a phosphoric acid ester or a salt thereof according to claim 1, wherein polyglycerin having a degree of condensation of 2 or more is reacted with a phosphorylating agent.
２記載の製造方法。3. The method according to claim 2, wherein the phosphorylating agent is polyphosphoric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14750591A JP2931932B2 (en) | 1991-06-19 | 1991-06-19 | Phosphate ester or salt thereof and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14750591A JP2931932B2 (en) | 1991-06-19 | 1991-06-19 | Phosphate ester or salt thereof and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH051081A true JPH051081A (en) | 1993-01-08 |
| JP2931932B2 JP2931932B2 (en) | 1999-08-09 |
Family
ID=15431887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14750591A Expired - Fee Related JP2931932B2 (en) | 1991-06-19 | 1991-06-19 | Phosphate ester or salt thereof and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2931932B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693318A (en) * | 1996-07-15 | 1997-12-02 | Basf Corporation | Stable salicylic acid and peroxide containing skin and hair cleanser composition |
| WO2001004250A1 (en) * | 1999-07-12 | 2001-01-18 | The Procter & Gamble Company | Polyhydroxyl/phosphate copolymers and compositions containing the same |
| JP2011001277A (en) * | 2009-06-17 | 2011-01-06 | Daicel Chemical Industries Ltd | New polyglycerol derivative or salt thereof, and method for producing the same |
-
1991
- 1991-06-19 JP JP14750591A patent/JP2931932B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693318A (en) * | 1996-07-15 | 1997-12-02 | Basf Corporation | Stable salicylic acid and peroxide containing skin and hair cleanser composition |
| WO2001004250A1 (en) * | 1999-07-12 | 2001-01-18 | The Procter & Gamble Company | Polyhydroxyl/phosphate copolymers and compositions containing the same |
| JP2011001277A (en) * | 2009-06-17 | 2011-01-06 | Daicel Chemical Industries Ltd | New polyglycerol derivative or salt thereof, and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2931932B2 (en) | 1999-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |