JP4543692B2 - Basic amino acid derivatives - Google Patents
Basic amino acid derivatives Download PDFInfo
- Publication number
- JP4543692B2 JP4543692B2 JP2004027873A JP2004027873A JP4543692B2 JP 4543692 B2 JP4543692 B2 JP 4543692B2 JP 2004027873 A JP2004027873 A JP 2004027873A JP 2004027873 A JP2004027873 A JP 2004027873A JP 4543692 B2 JP4543692 B2 JP 4543692B2
- Authority
- JP
- Japan
- Prior art keywords
- amino acid
- basic amino
- acid derivative
- general formula
- acid
- 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.)
- Expired - Lifetime
Links
- 150000003862 amino acid derivatives Chemical class 0.000 title claims description 37
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 13
- 239000003349 gelling agent Substances 0.000 claims description 13
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 11
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 description 51
- -1 alkali metal salts Chemical class 0.000 description 34
- 239000002609 medium Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000499 gel Substances 0.000 description 18
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- 229930195729 fatty acid Natural products 0.000 description 15
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- 229940024606 amino acid Drugs 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
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- 239000002699 waste material Substances 0.000 description 4
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- 229940114072 12-hydroxystearic acid Drugs 0.000 description 3
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
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- 239000004480 active ingredient Substances 0.000 description 3
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- 150000002739 metals Chemical class 0.000 description 3
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- 238000010998 test method Methods 0.000 description 3
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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- Cosmetics (AREA)
Description
本発明は、常温で液状を呈する様々な有機媒体等をゲル化または固化するのに有用な塩基性アミノ酸誘導体及びこれらの少なくとも１種を含有することを特徴とするゲル化剤、固化剤、ゲル及び香粧品に関する。 The present invention relates to a gelling agent, a solidifying agent, and a gel characterized by containing a basic amino acid derivative useful for gelling or solidifying various organic media that are liquid at room temperature, and at least one of them. And cosmetics.
常温で液状を呈する各種香粧品、医薬品、農薬、接着剤、樹脂、塗料等の流動性をコントロールすることにより、多様化した使用目的に合致した形態に加工する方法は産業上非常に重要な技術である。また、流出油事故による災害や海洋汚染は深刻な社会問題となっているが、油を固形化することができれば油の拡散のみならず容易かつ効率よく回収することが可能となり、流出油のゲル化処理は極めて有効な流出油防除手段となりうる。さらに、一般家庭からでる食用の廃油は水質汚染の原因となるが、廃油を簡便な方法でゲル化処理し固形物として廃棄することができれば環境への悪影響を低減できる。 A process that can be processed into various forms for various purposes by controlling the fluidity of various cosmetics, pharmaceuticals, agricultural chemicals, adhesives, resins, paints, etc. that are liquid at room temperature is a very important industrial technology. It is. In addition, disasters and marine pollution caused by spilled oil accidents have become serious social problems, but if the oil can be solidified, it becomes possible not only to diffuse the oil but also to collect it easily and efficiently. Treatment can be an extremely effective spill control method. Furthermore, edible waste oil from ordinary households causes water pollution, but if the waste oil can be gelled by a simple method and discarded as a solid, adverse environmental impacts can be reduced.
このような液状物質の流動性や粘度を制御する機能を有する物質としては、長鎖脂肪酸のアルカリ金属塩（特許文献１：特開昭５５−７５４９３号公報）、金属石けん（特許文献２：特公昭５９−５２１９６号公報）、１２−ヒドロキシステアリン酸（特許文献３：特公昭６０−４４９６８号公報）、多価アルコールとベンズアルデヒドの縮合物（特許文献４：特開昭５９−７７８５９号公報）、Ｎ−アシルアミノ酸アミド（特許文献５：特公昭５４−３３７９８号公報）等が知られていた。 Examples of such a substance having a function of controlling the fluidity and viscosity of a liquid substance include alkali metal salts of long chain fatty acids (Patent Document 1: Japanese Patent Laid-Open No. 55-75493), metal soap (Patent Document 2: Special). No. 59-52196), 12-hydroxystearic acid (Patent Document 3: Japanese Patent Publication No. 60-44968), condensate of polyhydric alcohol and benzaldehyde (Patent Document 4: JP-A 59-77859), N-acylamino acid amides (Patent Document 5: Japanese Patent Publication No. 54-33798) have been known.
この中で、長鎖脂肪酸のアルカリ金属塩や金属石けんは液状有機媒体をゲル化または固形化させるのに多量の添加量を必要とした。また、１２−ヒドロキシステアリン酸は、ゲル化できる有機媒体の種類が少なく、ゲル化能も低いため、得られたゲルは強度が弱く脆くて崩れやすく、常温付近でのゲル安定性に欠ける。一方、ジベンジリデンソルビトールに代表される多価アルコールとベンズアルデヒドの縮合物は、多くの有機媒体をゲル化させることが出来るが、溶解温度が高いため低沸点物質や熱に弱い物質と併用する場合に制限がある。また、縮合物中のアセタール部位が不安定で分解するという欠点を有する。Ｎ−ラウロイル−Ｌ−グルタミン酸−α、γ−ジ−ｎ−ブチルアミドに代表されるようなＮ−アシルアミノ酸アミドは少量の添加量で多くの有機媒体をゲル化または固化させることができ得られたゲルの強度も強いが、メタノールのような低級アルコールに対してはゲル化能が乏しく、必ずしも満足したゲル化性能を有していなかった。 Among these, long-chain fatty acid alkali metal salts and metal soaps require a large amount of addition to gel or solidify the liquid organic medium. In addition, 12-hydroxystearic acid has few types of organic media that can be gelled and has low gelling ability. Therefore, the obtained gel is weak and brittle and easily collapses, and lacks gel stability near room temperature. On the other hand, polyhydric alcohol and benzaldehyde condensates represented by dibenzylidene sorbitol can gel many organic media, but when used in combination with low-boiling substances or heat-sensitive substances because of their high melting temperatures. There is a limit. In addition, the acetal site in the condensate is unstable and decomposes. N-acylamino acid amide represented by N-lauroyl-L-glutamic acid-α, γ-di-n-butyramide was obtained by gelling or solidifying many organic media with a small addition amount. Although the strength of the gel is strong, the gelling ability is poor with respect to lower alcohols such as methanol, and the gelling performance is not always satisfactory.
上記のような欠点を改良するために、近年有機媒体のゲル化剤または固化剤の開発が活発に行われている。その一例として、シクロヘキサントリカルボキサミド（特許文献６：特開平１０−２７３４７７号公報）、ビス（アシルアミノ）シクロヘキサン誘導体（特許文献７：特開平１０−２３７０３４号公報）、オリゴペプタイドアルキルアミド誘導体（特許文献８：特開平１０−２４５３９６号公報、特許文献９：特開平１０−２２６６１４号公報）、ジアミノシクロヘキサンとアルキルイソシアネートを反応させて得られるジアルキルウレア誘導体（特許文献１０：特開平８−２３１９４２号公報）、環状ジペプチド（特許文献１１：特開平７−２４７４７４号公報、特許文献１２：特開平７−２４７４７３号公報）、Ｎα−アルキル若しくはアルケニルカルバモイル−Ｎω−アシルアミノ酸エステル化合物（特許文献１３：特開２０００-２５６３０３号公報）等が挙げられる。これらは、少量の添加量で多種多様の液状有機媒体をゲル化または固化でき、得られるゲルの強度も強く常温付近での安定性にも優れる。しかし一方では、ゲル化能が化合物の立体配置によって大きく左右され、特定の立体配置を有する原料の合成、分離が難しく原料の入手が困難であったり、製造面で反応のステップが多く工程が複雑であったり、生産性に問題がある。 In order to improve the above drawbacks, in recent years, development of organic medium gelling agents or solidifying agents has been actively conducted. Examples thereof include cyclohexanetricarboxamide (Patent Document 6: JP-A-10-273477), bis (acylamino) cyclohexane derivative (Patent Document 7: JP-A-10-237034), oligopeptide alkylamide derivative (Patent Document 8: JP-A-10-245396, Patent Document 9: JP-A-10-226614), dialkylurea derivatives obtained by reacting diaminocyclohexane and alkyl isocyanate (Patent Document 10: JP-A-8-231942), cyclic Dipeptide (Patent Document 11: JP-A-7-247474, Patent Document 12: JP-A-7-247473), Nα-alkyl or alkenylcarbamoyl-Nω-acylamino acid ester compound (Patent Document 13: JP2000-25) 303 JP), and the like. These are capable of gelling or solidifying a wide variety of liquid organic media with a small amount of addition, and the resulting gel has high strength and excellent stability near room temperature. However, on the other hand, the gelation ability is greatly influenced by the configuration of the compound, and it is difficult to synthesize and separate the raw material having a specific configuration, making it difficult to obtain the raw material, and there are many reaction steps in terms of production and the process is complicated. Or there is a problem with productivity.
さらには低級アルコール、塩素系溶剤、炭化水素油と、幅広い有機媒体のゲル化剤または固化剤としてＮα−アルキル若しくはアルケニルカルバモイル−Ｎω−アシルアミノ酸エステル化合物（特許文献１３：特開２０００−２５６３０３号公報）が開示されているが、それでも炭化水素油に比べ、低級アルコールや塩素系溶剤等に対するゲル化能が低い等、有機媒体の種類によってゲル化能にバラツキが見られた。 Furthermore, Nα-alkyl or alkenylcarbamoyl-Nω-acylamino acid ester compounds as gelling agents or solidifying agents for a wide range of organic media, including lower alcohols, chlorinated solvents, hydrocarbon oils (Patent Document 13: JP 2000-256303 A) However, gelation ability varies depending on the type of organic medium, such as lower gelation ability with respect to lower alcohols, chlorinated solvents, and the like than hydrocarbon oils.
本発明は広範な種類の液状有機媒体又は液状水媒体を少量の添加量でゲル化または固化させることが可能であり、更に簡便な方法で製造できるゲル化または固化剤を提供することを課題とする。 It is an object of the present invention to provide a gelling or solidifying agent capable of gelling or solidifying a wide variety of liquid organic media or liquid aqueous media with a small addition amount and capable of being produced by a simpler method. To do.
本発明者は、上述の問題点を解決するために鋭意検討を重ねた結果、下記一般式（１）で示される塩基性アミノ酸誘導体が、多種多様の液状有機媒体又は液状水媒体に対して優れたゲル化能力を有し、かつ簡便な方法で合成可能であることを見いだし、本発明を完成するに至った。すなわち本発明は、次の通りである。 As a result of intensive studies in order to solve the above-mentioned problems, the present inventors have found that the basic amino acid derivative represented by the following general formula (1) is superior to a wide variety of liquid organic media or liquid aqueous media. The present invention has been completed by finding that it has a gelling ability and can be synthesized by a simple method. That is, the present invention is as follows.
〔１〕 下記一般式（１）で示される塩基性アミノ酸誘導体。
Ｒ1、Ｒ2は、各々独立で炭素原子数が５〜２１の直鎖もしくは分岐鎖のアルキル基またはアルケニル基であり、
Ｒ3、Ｒ4は、各々独立で炭素原子数が１〜２２のアルキル基もしくはアルケニル基、水素原子、アルカリ金属、またはアルカリ土類金属であり、前記アルキル基またはアルケニル基は、直鎖でもよく、分岐鎖を有していてもよく、環構造を有していてもよく、
ｚは０以上の整数であり、
ｘ、ｙは２〜４の整数である。）
〔２〕 前記一般式（１）のｚが０〜１０である、上記〔１〕に記載の塩基性アミノ酸誘導体。
〔３〕 塩基性アミノ酸誘導体として、前記一般式（１）のｚが０である、上記〔１〕に記載の塩基性アミノ酸誘導体。
〔４〕 塩基性アミノ酸誘導体として、上記一般式（１）のＲ1、Ｒ2が炭素原子数１１の直鎖アルキル基である、上記〔１〕に記載の塩基性アミノ酸誘導体。
〔５〕 上記一般式（１）のＲ3、Ｒ4がアルカリ金属またはアルカリ土類金属である、上記〔１〕に記載の塩基性アミノ酸誘導体。
〔６〕 上記〔１〕に記載の塩基性アミノ酸誘導体の少なくとも１種を含有することを特徴とするゲル化剤または固化剤。
〔７〕 上記〔１〕に記載の塩基性アミノ酸誘導体の少なくとも１種を含有することを特徴とするゲル。
〔８〕 上記〔１〕に記載の塩基性アミノ酸誘導体の少なくとも１種を含有することを特徴とする香粧品。
[1] A basic amino acid derivative represented by the following general formula (1).
R 1 and R 2 are each independently a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms,
R 3 and R 4 are each independently an alkyl group or alkenyl group having 1 to 22 carbon atoms, a hydrogen atom, an alkali metal, or an alkaline earth metal, and the alkyl group or alkenyl group may be linear. , May have a branched chain, may have a ring structure,
z is an integer greater than or equal to 0,
x and y are integers of 2 to 4. )
[2] The basic amino acid derivative according to [1], wherein z in the general formula (1) is 0 to 10.
[3] The basic amino acid derivative according to the above [1], wherein z in the general formula (1) is 0.
[4] The basic amino acid derivative according to [1], wherein R 1 and R 2 in the general formula (1) are linear alkyl groups having 11 carbon atoms as the basic amino acid derivative.
[5] The basic amino acid derivative according to the above [1], wherein R 3 and R 4 in the general formula (1) are an alkali metal or an alkaline earth metal.
[6] A gelling agent or a solidifying agent comprising at least one basic amino acid derivative according to [1] above.
[7] A gel comprising at least one basic amino acid derivative according to the above [1].
[8] A cosmetic comprising at least one of the basic amino acid derivatives according to [1].
本発明によれば、上記一般式（１）で示される塩基性アミノ酸誘導体を用いて広範な種類の液状有機媒体を少量の添加量でゲル化または固化させることが可能である。特にナトリウム、カリウム等のアルカリ金属、マグネシウム、カルシウム等のアルカリ土類金属またはこれらの混合金属の場合には、液状有機媒体のみならず、液状水媒体をもゲル化させられる。また、本発明によれば、簡便な方法で合成できるゲル化または固化剤が提供される。さらに、本発明の塩基性アミノ酸誘導体を用いて形成されるゲル化物は常温付近での長期安定性に優れる。 According to the present invention, a wide variety of liquid organic media can be gelled or solidified with a small amount of addition using the basic amino acid derivative represented by the general formula (1). In particular, in the case of alkali metals such as sodium and potassium, alkaline earth metals such as magnesium and calcium, or mixed metals thereof, not only a liquid organic medium but also a liquid aqueous medium can be gelled. The present invention also provides a gelling or solidifying agent that can be synthesized by a simple method. Furthermore, the gelled product formed using the basic amino acid derivative of the present invention is excellent in long-term stability near normal temperature.
本発明は、液状を呈する香粧品、医薬品、農薬、接着剤、樹脂、塗料等に例示される液状有機媒体又は液状水媒体を含む製品群の製造・加工において、液状有機媒体又は液状水媒体の流動性をコントロールし、各製品に応じ多様化した使用目的に合致するように加工するために有用である。また、本発明は、海洋などにおける流出油のゲル化処理、一般家庭から排出される廃油のゲル化処理など環境保全分野においても好ましく適用可能である。 The present invention relates to a liquid organic medium or liquid aqueous medium in the production and processing of a liquid organic medium or liquid aqueous medium exemplified by liquid cosmetics, pharmaceuticals, agricultural chemicals, adhesives, resins, paints, etc. It is useful for controlling fluidity and processing to meet diversified use purposes according to each product. In addition, the present invention is preferably applicable in the field of environmental conservation such as gelation of spilled oil in the ocean and the like, and gelation of waste oil discharged from ordinary households.
本発明は、上記一般式（１）で示される塩基性アミノ酸誘導体と、これを有効成分とするゲル化剤または固化剤と、これを含有するゲルおよび香粧品とを提供する。なお、上記一般式（１）で示される化合物は、双頭型塩基性アミノ酸誘導体ともいう。 The present invention provides a basic amino acid derivative represented by the above general formula (1), a gelling agent or a solidifying agent containing this as an active ingredient, and a gel and cosmetic containing the same. The compound represented by the general formula (1) is also referred to as a double-headed basic amino acid derivative.
Ｒ1、Ｒ2は各々独立に炭素原子数が５〜２１の直鎖もしくは分岐鎖のアルキル基またはアルケニル基である。Ｒ1、Ｒ2の炭素原子数は好ましくは７〜１１である。 R 1 and R 2 are each independently a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms. The number of carbon atoms of R 1 and R 2 is preferably 7-11.
Ｒ3、Ｒ4は各々独立で炭素原子数が１〜２２のアルキル基、アルケニル基、水素原子、アルカリ金属、またはアルカリ土類金属である。前記アルキル基またはアルケニル基の構造は、直鎖でもよいし、分岐鎖を備えていてもよいし、また、環構造を備えるものであってもよい。ゲル化能の点からすると、分岐を有していることが好ましく、他方、直鎖の場合には、炭素原子数は少ないほど好ましい傾向がある。また、前記アルカリ金属はナトリウム、カリウム又はこれらの混合物とすることができ、前記アルカリ土類金属はマグネシウム、カルシウム又はこれらの混合物とすることができる。 R 3 and R 4 are each independently an alkyl group, alkenyl group, hydrogen atom, alkali metal, or alkaline earth metal having 1 to 22 carbon atoms. The structure of the alkyl group or alkenyl group may be a straight chain, a branched chain, or a ring structure. From the viewpoint of gelling ability, it is preferable to have a branch. On the other hand, in the case of a straight chain, the smaller the number of carbon atoms, the better. The alkali metal may be sodium, potassium or a mixture thereof, and the alkaline earth metal may be magnesium, calcium or a mixture thereof.
ｚは０以上の整数であり、より好ましくは０〜１０であり、特に好ましくは０である。
本発明の塩基性アミノ酸誘導体は、前述のＮω−アシルアミノ酸とアルコールと両末端にカルボキシル基を有する脂肪酸の酸クロライドを原料とし、一般に公知慣用の手法により合成することができる。例えば、先ずＮω−アシルアミノ酸のカルボン酸部のエステル化を触媒の存在下、もしくは無触媒下でアルコールとの加熱（常圧、減圧）脱水縮合反応、エステル交換反応、共沸脱水縮合反応等のエステル化反応に準じて行った後、生成したＮω−アシルアミノ酸エステル化合物と１／２当量の両末端にカルボキシル基を有する脂肪酸の酸クロライドを不活性溶媒中で触媒の存在下、もしくは無触媒下で反応させることにより合成することができる。もちろん、これらの方法によらずとも、先にＮω−アシルアミノ酸と両末端にカルボキシル基を有する脂肪酸の酸クロライドを反応させ、次いでこれをエステル化する方法であっても何等差し支えない。またエステル化されていなくても構わない。
z is an integer greater than or equal to 0, More preferably, it is 0-10, Most preferably, it is 0.
The basic amino acid derivative of the present invention can be synthesized by generally known and commonly used methods using the above-mentioned Nω-acylamino acid, an alcohol and an acid chloride of a fatty acid having a carboxyl group at both ends as raw materials. For example, first, esterification of the carboxylic acid part of Nω-acylamino acid is carried out by heating (normal pressure, reduced pressure) dehydration condensation reaction, transesterification reaction, azeotropic dehydration condensation reaction with alcohol in the presence or absence of a catalyst. After carrying out according to the esterification reaction, the produced Nω-acylamino acid ester compound and 1/2 equivalent of an acid chloride of a fatty acid having a carboxyl group at both ends are present in an inert solvent in the presence or absence of a catalyst. It can synthesize | combine by making it react with. Of course, even if these methods are not used, there is no problem even if the Nω-acylamino acid is first reacted with an acid chloride of a fatty acid having a carboxyl group at both ends and then esterified. Moreover, it does not need to be esterified.
上記方法で得た塩基性アミノ酸誘導体を、更にアルカリ金属水酸化物、アルカリ土類金属水酸化物等と反応させて、そのR3及びR4部分をアルカリ金属及び／又はアルカリ土類金属で置換することにより、R3及びR4がアルカリ金属及び／又はアルカリ土類金属である塩基性アミノ酸誘導体に変換することができる。 The basic amino acid derivative obtained by the above method is further reacted with an alkali metal hydroxide, an alkaline earth metal hydroxide or the like, and the R 3 and R 4 portions thereof are replaced with an alkali metal and / or an alkaline earth metal. By doing so, R 3 and R 4 can be converted into a basic amino acid derivative in which alkali metal and / or alkaline earth metal is used.
このようにして得られた反応生成物中には未反応の原料が残存する場合もあるが、抽出、再結晶、クロマトグラフィー等の公知の方法により精製することができる。なお、ゲル化能に影響がない場合は、混合物のまま使用してもよい。 Although unreacted raw materials may remain in the reaction product thus obtained, the reaction product can be purified by a known method such as extraction, recrystallization, or chromatography. In addition, when there is no influence on gelation ability, you may use it as a mixture.
Ｎω−アシルアミノ酸としては、Ｎε−アシルリジン、Ｎδ−アシルオルニチン、Ｎγ−アシル−α、γ−ジアミノ酪酸が挙げられ、この中で、Ｎε−アシルリジンが最も好ましい。 Examples of Nω-acylamino acids include Nε-acyl lysine, Nδ-acylornithine, Nγ-acyl-α, and γ-diaminobutyric acid. Among them, Nε-acyl lysine is most preferable.
Ｎω−アシルアミノ酸のアシル基（Ｒ1とＲ2）としては、炭素原子数５〜２１の直鎖若しくは分岐鎖の飽和若しくは不飽和の脂肪酸より誘導されるアシル基が好ましく、例えば、オクタン酸、デカン酸、ラウリン酸、パルミチン酸、ステアリン酸、オレイン酸等の長鎖アシル基が挙げられる。アシル基の炭素数が、２２より大きい場合はゲル化能が乏しくなる場合があり、適当でない。 The acyl group (R 1 and R 2 ) of the Nω-acylamino acid is preferably an acyl group derived from a linear or branched saturated or unsaturated fatty acid having 5 to 21 carbon atoms, such as octanoic acid, Long chain acyl groups such as decanoic acid, lauric acid, palmitic acid, stearic acid, oleic acid and the like can be mentioned. If the number of carbon atoms in the acyl group is greater than 22, the gelling ability may be poor, which is not appropriate.
Ｎω−アシルアミノ酸は、例えば塩基性アミノ酸と長鎖脂肪酸とを加熱脱水することにより容易に合成できる。工業的に入手可能なＮω−アシルアミノ酸としては、例えば味の素（株）製のアミホープＬＬ（Ｎε−ラウロイル−Ｌ−リジン）等が挙げられる。 Nω-acylamino acids can be easily synthesized, for example, by heat dehydration of basic amino acids and long chain fatty acids. Examples of industrially available Nω-acylamino acids include Amihope LL (Nε-lauroyl-L-lysine) manufactured by Ajinomoto Co., Inc.
Ｎω−アシルアミノ酸は、光学活性体またはラセミ体のいずれであっても差し支えないが、ゲル化能が向上するという観点で、光学活性体の方が好ましい。また、これらは単独で使用してもよく、２種以上を混合して使用してもよい。 The Nω-acylamino acid may be either an optically active form or a racemic form, but the optically active form is preferred from the viewpoint of improving gelation ability. Moreover, these may be used independently and may mix and use 2 or more types.
Ｎω−アシルアミノ酸のエステル化に使用されるアルコール（Ｒ3とＲ4）としては、炭素数１〜２２の直鎖若しくは分岐鎖の飽和若しくは不飽和及び／または環状を有するアルコールで、例えばメタノール、エタノール、ｎ−プロパノール、イソプロパノール、ｎ−ブタノール、２−ブタノール、ｎ−ペンタノール、ｎ−ヘキサノール、シクロヘキサノール、ｎ−ヘプタノール、ｎ−オクタノール、２−エチルヘキサノール、ｎ−ノナノール、ｎ−デカノール、ラウリルアルコール、ミリスチルアルコール、パルミチルアルコール、ステアリルアルコール、オレイルアルコール、イソステアリルアルコール、ベヘニルアルコール、２−オクチルドデカノール等が挙げられる。またエステル化されていなくても構わない。さらに、炭素数が２２を越える場合は、ゲル化能力が乏しくなる場合があり、適当でない。 Alcohols (R 3 and R 4 ) used for esterification of Nω-acylamino acid are straight-chain or branched-chain saturated or unsaturated and / or cyclic alcohols having 1 to 22 carbon atoms, such as methanol, Ethanol, n-propanol, isopropanol, n-butanol, 2-butanol, n-pentanol, n-hexanol, cyclohexanol, n-heptanol, n-octanol, 2-ethylhexanol, n-nonanol, n-decanol, lauryl Examples include alcohol, myristyl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, behenyl alcohol, 2-octyldodecanol and the like. Moreover, it does not need to be esterified. Furthermore, when the number of carbon atoms exceeds 22, the gelation ability may become poor and is not appropriate.
また、本発明の塩基性アミノ酸誘導体のカルボン酸中和塩として利用される金属（Ｒ3とＲ4）としては、ナトリウム、カリウム等のアルカリ金属、マグネシウム、カルシウム等のアルカリ土類金属またはこれらの混合金属等が挙げられる。液状有機媒体及び液状水媒体ともにゲル化させるという観点からアルカリ金属塩が好ましく、ゲル強度という観点からモノアルカリ金属塩が特に好ましい。 In addition, as the metal (R 3 and R 4 ) used as the carboxylic acid neutralized salt of the basic amino acid derivative of the present invention, alkali metals such as sodium and potassium, alkaline earth metals such as magnesium and calcium, and these metals A mixed metal etc. are mentioned. Alkali metal salts are preferred from the viewpoint of gelling both the liquid organic medium and the liquid aqueous medium, and monoalkali metal salts are particularly preferred from the viewpoint of gel strength.
２分子のＮω−アシルアミノ酸アルキルエステルと両末端にカルボキシル基を有する脂肪酸の酸クロライドとの反応に使用されるジカルボン酸クロライドとしては、特に限定されないが、例えばオギザリルクロライド、マロニルクロライド、スクシニルクロライド、グルタリルクロライド、アジポイルクロライド、ピメロイルクロライド、スベロイルクロライド、アゼラオイルクロライド、セバコイルクロライド、ドデカンジオイルクロライド等が挙げられる。メチレン鎖の炭素数（ｚ）が０〜１０であるものが好ましく、０であるものが最も好ましい。これらは単独で使用してもよく、または２種以上を混合して使用してもよい。 The dicarboxylic acid chloride used in the reaction of two molecules of Nω-acylamino acid alkyl ester and an acid chloride of a fatty acid having a carboxyl group at both ends is not particularly limited, but examples thereof include oxalyl chloride, malonyl chloride, succinyl chloride, Examples include glutaryl chloride, adipoyl chloride, pimeloyl chloride, suberoyl chloride, azela oil chloride, sebacoyl chloride, and dodecanedioyl chloride. The methylene chain preferably has 0 to 10 carbon atoms (z), and most preferably 0. These may be used alone or in combination of two or more.
本発明はさらに、上記一般式（１）で示される塩基性アミノ酸誘導体を有効成分とするゲル化剤または固化剤を提供する。本発明のゲル化剤または固化剤には、上記本発明の塩基性アミノ酸誘導体の少なくとも１種が有効成分として用いられていればよく、２種以上が混合されたものであってもよい。また、本発明のゲル化剤または固化剤には、本発明の効果を損なわない範囲で、他のゲル化剤または固化剤を添加してもよい。他のゲル化剤または固化剤としては、例えば、Ｎ−アシル−Ｌ−グルタミン酸ジアルキルアミド、ポリアミド樹脂、１２−ヒドロキシステアリン酸、ステアリン酸ナトリウム、ジベンジリデン−Ｄ−ソルビトール、脂肪酸デキストリン、ゼラチン等が挙げられる。さらに、本発明のゲル化剤または固化剤には、基材、補助剤などの他の成分が含まれていてもよい。他の成分としては、界面活性剤、添加剤、粉体などが例示される。 The present invention further provides a gelling agent or solidifying agent containing the basic amino acid derivative represented by the general formula (1) as an active ingredient. In the gelling agent or solidifying agent of the present invention, at least one of the above basic amino acid derivatives of the present invention may be used as an active ingredient, and two or more of them may be mixed. Moreover, you may add another gelatinizer or solidification agent to the gelatinizer or solidification agent of this invention in the range which does not impair the effect of this invention. Examples of other gelling agents or solidifying agents include N-acyl-L-glutamic acid dialkylamide, polyamide resin, 12-hydroxystearic acid, sodium stearate, dibenzylidene-D-sorbitol, fatty acid dextrin, gelatin and the like. It is done. Furthermore, the gelling agent or solidifying agent of the present invention may contain other components such as a substrate and an auxiliary agent. Examples of other components include surfactants, additives, and powders.
各種界面活性剤としては、例えば、Ｎ−長鎖アシル酸性アミノ酸塩やＮ−長鎖アシル中性アミノ酸塩などのＮ−長鎖アシルアミノ酸塩、Ｎ−長鎖脂肪酸アシル−Ｎ−メチルタウリン塩、アルキルサルフェートおよびそのアルキレンオキシド付加物、脂肪酸アミドエーテルサルフェート、脂肪酸の金属塩および弱塩基塩、スルホコハク酸系界面活性剤、アルキルフォスフェートおよびそのアルキレンオキシド付加物、アルキルエーテルカルボン酸、等のアニオン界面活性剤；グリセリンエーテルおよびそのアルキレンオキシド付加物などのエーテル型界面活性剤、グリセリンエステルおよびそのアルキレンオキシド付加物などのエステル型界面活性剤、ソルビタンエステルおよびそのアルキレンオキシド付加物などのエーテルエステル型界面活性剤、ポリオキシアルキレン脂肪酸エステル、グリセリンエステル、脂肪酸ポリグリセリンエステル、ソルビタンエステル、ショ糖脂肪酸エステルなどのエステル型界面活性剤、アルキルグルコシド類、硬化ヒマシ油ピログルタミン酸ジエステルおよびそのエチレンオキシド付加物、ならびに脂肪酸アルカノールアミドなどの含窒素型の非イオン性界面活性剤、等の非イオン性界面活性剤；アルキルアンモニウムクロライド、ジアルキルアンモニウムクロライドなどの脂肪族アミン塩、それらの４級アンモニウム塩、ベンザルコニウム塩などの芳香族４級アンモニウム塩、脂肪酸アシルアルギニンエステル、等のカチオン界面活性剤；並びにカルボキシベタインなどのベタイン型界面活性剤、アミノカルボン酸型界面活性剤、イミダゾリン型界面活性剤、等の両性界面活性剤；等が挙げられる。 Examples of the various surfactants include N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts, N-long chain fatty acid acyl-N-methyl taurine salts, Anionic surfactants such as alkyl sulfates and their alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak base salts, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, alkyl ether carboxylic acids, etc. Agents; ether type surfactants such as glycerin ether and its alkylene oxide adduct, ester type surfactants such as glycerin ester and its alkylene oxide adduct, ether ester type surface activity such as sorbitan ester and its alkylene oxide adduct Agent, polyoxyalkylene fatty acid ester, glycerin ester, fatty acid polyglycerin ester, sorbitan ester, sucrose fatty acid ester and other ester type surfactants, alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and its ethylene oxide adduct, and fatty acid alkanol Nonionic surfactants such as nitrogen-containing nonionic surfactants such as amides; aliphatic amine salts such as alkylammonium chloride and dialkylammonium chloride, quaternary ammonium salts thereof, benzalkonium salts and the like Cationic surfactants such as aromatic quaternary ammonium salts and fatty acid acyl arginine esters; and betaine type surfactants such as carboxybetaine, aminocarboxylic acid type surfactants, imidazoline type Surface active agents, amphoteric surface active agents and the like; and the like.
各種添加剤としては、例えば、グリシン、Ｌ−アラニン、ＤＬ−アラニン、セリン、スレオニン、アルギニン、グルタミン酸、アスパラギン酸、ロイシン、バリンなどのアミノ酸類；グリセリン、エチレングリコール、１，３−ブチレングリコール、プロピレングリコール、イソプレングリコールなどの多価アルコール；ポリグルタミン酸、ポリアスパラギン酸を含むポリアミノ酸およびその塩、ポリエチレングリコール、アラビアゴム類、アルギン酸塩、キサンタンガム、ヒアルロン酸、ヒアルロン酸塩、キチン、キトサン、水溶性キチン、カルボキシビニルポリマー、カルボキシメチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルトリメチルアンモニウムクロライド、ポリ塩化ジメチルメチレンピペリジウム、ポリビニルピロリドン誘導体四級アンモニウム、カチオン化プロテイン、コラーゲン分解物およびその誘導体、アシル化タンパク、ポリグリセリン、などの水溶性高分子；マンニトールなどの糖アルコールおよびそのアルキレンオキシド付加物；エタノール、プロパノールなどの低級アルコール等の他、動植物抽出物、核酸、ビタミン、酵素、抗炎症剤、殺菌剤、防腐剤、抗酸化剤、紫外線吸収剤、キレート剤、制汗剤、顔料、色素、酸化染料、有機及び無機粉体、ｐＨ調整剤、パール化剤、湿潤剤等を挙げることができる。 Examples of various additives include amino acids such as glycine, L-alanine, DL-alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine, and valine; glycerin, ethylene glycol, 1,3-butylene glycol, propylene Polyhydric alcohols such as glycol and isoprene glycol; polyamino acids including polyglutamic acid and polyaspartic acid and salts thereof, polyethylene glycol, gum arabic, alginate, xanthan gum, hyaluronic acid, hyaluronate, chitin, chitosan, water-soluble chitin , Carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, polydimethylmethylenepiperidinium chloride, polybiphenyl Water-soluble polymers such as rupyrrolidone derivative quaternary ammonium, cationized protein, collagen degradation product and derivatives thereof, acylated protein, polyglycerin, etc .; sugar alcohols such as mannitol and alkylene oxide adducts thereof; lower grades such as ethanol and propanol In addition to alcohol, etc., animal and plant extracts, nucleic acids, vitamins, enzymes, anti-inflammatory agents, bactericides, antiseptics, antioxidants, UV absorbers, chelating agents, antiperspirants, pigments, dyes, oxidation dyes, organic and inorganic Examples thereof include powders, pH adjusting agents, pearling agents, wetting agents and the like.
各種粉体としては、例えば、ナイロンビーズ、シリコーンビーズ等の樹脂粉体、ナイロンパウダー、金属脂肪酸石鹸、黄酸化鉄、赤色酸化鉄、黒酸化鉄、酸化クロム、酸化コバルト、カーボンブラック、群青、紺青、酸化亜鉛、酸化チタン、酸化ジルコニウム、酸化珪素、酸化アルミニウム、酸化セリウム、雲母チタン、窒化ホウ素、硫酸バリウム、炭酸カルシウム、炭酸マグネシウム、珪酸アルミニウム、珪酸マグネシウム、炭化珪素、色素、レーキ、セリサイト、マイカ、タルク、カオリン、板状硫酸バリウム、バタフライ状硫酸バリウム、微粒子酸化チタン、微粒子酸化亜鉛、微粒子酸化鉄、アシルリジン、アシルグルタミン酸、アシルアルギニン、アシルグリシン等のアシルアミノ酸等が挙げられ、更にシリコーン処理、フッ素化合物処理、シランカップリング剤処理、シラン処理有機チタネート処理、アシル化リジン処理、脂肪酸処理、金属石鹸処理、油剤処理、アミノ酸処理等の表面処理が施してあっても構わない。 Examples of various powders include resin powders such as nylon beads and silicone beads, nylon powder, metal fatty acid soap, yellow iron oxide, red iron oxide, black iron oxide, chromium oxide, cobalt oxide, carbon black, ultramarine, and bitumen , Zinc oxide, titanium oxide, zirconium oxide, silicon oxide, aluminum oxide, cerium oxide, titanium mica, boron nitride, barium sulfate, calcium carbonate, magnesium carbonate, aluminum silicate, magnesium silicate, silicon carbide, dye, lake, sericite, Examples include mica, talc, kaolin, plate-like barium sulfate, butterfly-like barium sulfate, fine particle titanium oxide, fine particle zinc oxide, fine particle iron oxide, acyl lysine, acyl glutamic acid, acyl arginine, acyl glycine and other acyl amino acids. , Fluorinated compounds Treatment, silane coupling agent treatment, silane treatment organic titanate process, acylated lysine treatment, fatty acid treatment, metal soap treatment, oil treatment, may be each other by subjecting the surface treatment of the amino acid treatment or the like.
本発明の塩基性アミノ酸誘導体は広範な種類の液状有機媒体を少量の添加量でゲル化または固化させる作用に優れる。ここでいう液状有機媒体としては、例えばガソリン、灯油、軽油、重油等の鉱物油；鯨油、ニシン油等の動物油；大豆油、オリーブ油、ヒマシ油、アマニ油、コーン油、ヒマワリ油、ナタネ油、綿実油等の植物油；石油ベンジン、流動パラフィン、ベンゼン、トルエン、ヘキサン、シクロヘキサン等の炭化水素類；酢酸エチル、酢酸ブチル、酢酸アミル、セバシン酸ジエチル、セバシン酸ジオクチル、フタル酸ジエチル、フタル酸ジオクチル、ポリオキシアルキレングリコール脂肪酸エステル等のエステル類；ジグライム、ポリアルキレングリコールエーテル等のエーテル類； ＴＨＦ、ジオキサン等の環状エーテル類；アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン、アニスアルデヒド等のケトン、アルデヒド類；メタノール、エタノール、プロパノール、ブタノール等の低級アルコール類；メチルポリシロキサン、メチルフェニルポリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン等のシリコン油類；クロロベンゼン、四塩化炭素等のハロゲン類； ＤＭＦ、ＤＭＳＯ等の高極性有機溶剤等、可燃性、不燃性の液状有機媒体の種類を問わず極めて広範囲に有効であり、これらの液状有機媒体が混合されたもの及び主成分である媒体に対しても有効である。また、液状有機媒体は完全溶解状態でも懸濁状態でも構わない。なお、前記液状有機媒体は、本発明の効果を妨げない範囲内において、液状水媒体を含有させることができる。ここでいう液状水媒体としては、例えば水、有機性塩或は無機性塩含有水溶液等である。 The basic amino acid derivative of the present invention is excellent in the action of gelling or solidifying a wide variety of liquid organic media with a small addition amount. Examples of the liquid organic medium include mineral oils such as gasoline, kerosene, light oil and heavy oil; animal oils such as whale oil and herring oil; soybean oil, olive oil, castor oil, linseed oil, corn oil, sunflower oil, rapeseed oil, Vegetable oil such as cottonseed oil; petroleum benzine, liquid paraffin, benzene, toluene, hexane, cyclohexane and other hydrocarbons; ethyl acetate, butyl acetate, amyl acetate, diethyl sebacate, dioctyl sebacate, diethyl phthalate, dioctyl phthalate, poly Esters such as oxyalkylene glycol fatty acid esters; Ethers such as diglyme and polyalkylene glycol ethers; Cyclic ethers such as THF and dioxane; Ketones and aldehydes such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone and anisaldehyde Lower alcohols such as methanol, ethanol, propanol and butanol; silicone oils such as methylpolysiloxane, methylphenylpolysiloxane, octamethylcyclotetrasiloxane and decamethylcyclopentasiloxane; halogens such as chlorobenzene and carbon tetrachloride A highly polar organic solvent such as DMF, DMSO, etc., which is effective over a wide range regardless of the type of flammable or non-flammable liquid organic medium. Also effective. The liquid organic medium may be completely dissolved or suspended. The liquid organic medium can contain a liquid aqueous medium as long as the effects of the present invention are not hindered. Examples of the liquid aqueous medium here include water, an organic salt or an aqueous solution containing an inorganic salt.
本発明の塩基性アミノ酸誘導体において前記R3及びR4がいずれもナトリウム、カリウム等のアルカリ金属、マグネシウム、カルシウム等のアルカリ土類金属、またはこれらの混合金属の場合には、液状有機媒体のみならず、液状水媒体をも良好にゲル化させられるという点において特に好ましい。ここでいう液状水媒体としては、例えば水、有機性塩或は無機性塩含有水溶液等である。なお、前記液状水媒体には、本発明の効果を妨げない範囲内において、液状有機媒体を含有させることができる。水と容易に溶け合うという観点で液状水溶性有機媒体が好ましい。液状水溶性有機媒体としては、例えばメタノール、エタノール、プロパノール、ブタノール等の低級アルコール類；エチレングリコール、プロピレングリコール、グリセリン、１，３−ブチレングリコール、ポリエチレングリコール等の多価アルコール等が挙げられる。 In the basic amino acid derivative of the present invention, when R 3 and R 4 are both alkali metals such as sodium and potassium, alkaline earth metals such as magnesium and calcium, or mixed metals thereof, only the liquid organic medium can be used. Furthermore, it is particularly preferable in that the liquid aqueous medium can be gelled well. Examples of the liquid aqueous medium here include water, an organic salt or an aqueous solution containing an inorganic salt. The liquid aqueous medium can contain a liquid organic medium as long as the effects of the present invention are not hindered. A liquid water-soluble organic medium is preferable from the viewpoint of easily dissolving with water. Examples of the liquid water-soluble organic medium include lower alcohols such as methanol, ethanol, propanol, and butanol; polyhydric alcohols such as ethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, and polyethylene glycol.
本発明の塩基性アミノ酸誘導体を液状有機媒体又は液状水媒体に添加し、必要に応じて５０〜１２０℃程度に均一状態になるよう加熱攪拌した後、常温にて静置することにより、ゲル化物または固化物を調製することができる。本発明の化合物の使用量としては、ゲル化または固化せしめる液状有機媒体又は液状水媒体の種類にもよるが、液状媒体１０００重量部に対し、１〜４００重量部、好ましくは１〜２００重量部で、より好ましくは１〜１００重量部、更に好ましくは２〜８０重量部である。使用量が１重量部より少ないと十分にゲル化せず、４００重量部より多いとゲル化する際ゲル化剤の一部が結晶化し析出するため不均一状態となり、外観不良や安定したゲル強度が保てず適当でない。また、固形化物の固さは本発明の化合物の添加量によって自由に調節することができる。 The basic amino acid derivative of the present invention is added to a liquid organic medium or a liquid aqueous medium, heated and stirred so as to be in a uniform state at about 50 to 120 ° C., if necessary, and then allowed to stand at room temperature, whereby a gelled product is obtained. Alternatively, a solidified product can be prepared. The amount of the compound of the present invention is 1 to 400 parts by weight, preferably 1 to 200 parts by weight with respect to 1000 parts by weight of the liquid medium, although it depends on the type of liquid organic medium or liquid aqueous medium to be gelled or solidified. More preferably, it is 1-100 weight part, More preferably, it is 2-80 weight part. If the amount used is less than 1 part by weight, it does not gel sufficiently, and if it exceeds 400 parts by weight, part of the gelling agent crystallizes and precipitates when gelling, resulting in a non-uniform state, poor appearance and stable gel strength. Is not appropriate. Further, the hardness of the solidified product can be freely adjusted by the amount of the compound of the present invention added.
従って、本発明における塩基性アミノ酸誘導体は工業的に製造されている入手が容易な原料から簡便な方法で合成できる。また、本発明の塩基性アミノ酸誘導体を、上述のような液状有機媒体又は液状水媒体を含有する香粧品、医薬品、農薬、接着剤、樹脂、塗料等に添加することによりこれらの流動性をコントロール、すなわちゲルを形成することが可能である。また、本発明は、海洋などにおける流出油のゲル化処理、一般家庭から排出される廃油のゲル化処理など環境保全分野においても好ましく適用可能である。特にアミノ酸系素材であるという観点で香粧品への適用が好ましい。香粧品としては、特に限定されないが、例えば、ゲル状化粧料、パック化粧料、粒状化粧料、スティック状化粧品、ゲル状芳香剤などが挙げられる。 Therefore, the basic amino acid derivative in the present invention can be synthesized by a simple method from industrially produced raw materials that are easily available. In addition, the basic amino acid derivative of the present invention is added to cosmetics, pharmaceuticals, agricultural chemicals, adhesives, resins, paints, and the like containing the liquid organic medium or liquid aqueous medium as described above to control their fluidity. That is, it is possible to form a gel. In addition, the present invention is preferably applicable in the field of environmental conservation such as gelation of spilled oil in the ocean and the like, and gelation of waste oil discharged from ordinary households. In particular, application to cosmetics is preferable from the viewpoint of being an amino acid-based material. Although it does not specifically limit as cosmetics, For example, gel-like cosmetics, pack cosmetics, granular cosmetics, stick-like cosmetics, gel-like fragrance | flavors, etc. are mentioned.
以下、実施例により本発明を具体的に説明するが、本発明はこれら実施例に限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples.
〔製造例１〕 ビス（Ｎε-ラウロイル-Ｌ-リジン）オギザリルアミドの合成
Ｎε−ラウロイル−Ｌ−リジン（アミホープＬＬ、味の素（株）製）１９．７１ｇ（６０ｍｍｏｌ）を２ｗｔ％のＮａＯＨ水溶液６００ｍｌに溶解し、エチルエーテルを加えた。新たに、蒸留したオギザリルクロライド３．８１ｇ（３０ｍｍｏｌ）をエーテル層にゆっくり加えた。この２層溶液を１時間ほど、０℃に保持したまま攪拌し、その後室温で２３時間攪拌した。得られた白色沈殿物を濾取し、水でよく洗い乾燥した。得られた粗生成物をメタノールーエーテルから２回再結晶することによって精製した。このものの元素分析、ＩＲ、ＮＭＲ等の示性値は構造を支持していた。ＩＲ測定結果を以下に示す。
ＩＲ測定結果（ＫＢｒ）：３３１７、１７３３、１６６１、１６４０、１５４１ｃｍ-1
[Production Example 1] Synthesis of bis (Nε-lauroyl-L-lysine) oxalilamide 19.71 g (60 mmol) of Nε-lauroyl-L-lysine (Amihop LL, manufactured by Ajinomoto Co., Inc.) was dissolved in 600 ml of 2 wt% NaOH aqueous solution. And ethyl ether was added. Freshly distilled oxalyl chloride 3.81 g (30 mmol) was slowly added to the ether layer. The two-layer solution was stirred for about 1 hour while maintaining at 0 ° C., and then stirred at room temperature for 23 hours. The resulting white precipitate was collected by filtration, washed well with water and dried. The resulting crude product was purified by recrystallization from methanol-ether twice. The elemental analysis, IR, NMR, etc. of this product supported the structure. The IR measurement results are shown below.
IR measurement result (KBr): 3317, 1733, 1661, 1640, 1541 cm −1
〔製造例２〕 ビス（Ｎε-ラウロイル-Ｌ-リジン−２−エチルヘキシル）オギザリルアミドの合成
Ｎε−ラウロイル−Ｌ−リジン２０ｇ（０．０６１ｍｏｌ）、９．５４ｍｌ（０．０６１ｍｏｌ）の２−エチルヘキサノール、２３．２ｇ（０．１２２ｍｏｌ）のｐ−トルエンスルホン酸１水和物を３００ｍｌのベンゼンと共にＤｅａｎ−Ｓｔａｒｋ装置を用い、油浴の温度を１３０℃にして２日間還流した。過剰のベンゼンを減圧除去して得られた残渣を１００ｍｌのＴＨＦに溶かし、３２ｇ／３２ｍｌ（０．２３０ｍｏｌ）のモルホリンを加え攪拌した。不溶物をろ過し、ろ液を冷凍庫に約１時間放置した。これをろ過し、減圧濃縮しジエチルエーテルを加えて振り混ぜ、この操作を2回繰り返した。これを減圧濃縮し、得られた残分を乾燥し、固形分２２．０４ｇを得た。
[Production Example 2] Synthesis of bis (Nε-lauroyl-L-lysine-2-ethylhexyl) oxalylamide Nε-lauroyl-L-lysine 20 g (0.061 mol), 9.54 ml (0.061 mol) of 2-ethylhexanol, 23.2 g (0.122 mol) of p-toluenesulfonic acid monohydrate was refluxed for 2 days using a Dean-Stark apparatus with 300 ml of benzene at an oil bath temperature of 130 ° C. Excess benzene was removed under reduced pressure, and the resulting residue was dissolved in 100 ml of THF, and 32 g / 32 ml (0.230 mol) of morpholine was added and stirred. Insoluble matter was filtered, and the filtrate was left in the freezer for about 1 hour. This was filtered, concentrated under reduced pressure, diethyl ether was added and shaken, and this operation was repeated twice. This was concentrated under reduced pressure, and the resulting residue was dried to obtain 22.04 g of a solid content.
上記固形分１２．３ｇを２００ｍｌの脱水ＴＨＦに溶かした。ここに、３０ｍｌ（０．０１４ｍｏｌ）の脱水トリエチルアミンを加えた。氷冷下、２ｍｌ（０．０２８ｍｏｌ）のオキザリルクロライドを加え、室温で一晩放置した。不溶のトリエチルアミン塩酸塩を自然濾過で除き、濾液を減圧濃縮した。得られた粗生成物はメタノールとジエチルエーテルから再結晶し、ビス（Ｎε-ラウロイル-Ｌ-リジン−２−エチルヘキシル）オギザリルアミド）を得た。
ＩＲ測定結果（ＫＢｒ）：３２９３、１７３６、１６４６、１５５２ｃｍ-1
The solid content of 12.3 g was dissolved in 200 ml of dehydrated THF. 30 ml (0.014 mol) of dehydrated triethylamine was added thereto. Under ice cooling, 2 ml (0.028 mol) of oxalyl chloride was added and left overnight at room temperature. Insoluble triethylamine hydrochloride was removed by natural filtration, and the filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized from methanol and diethyl ether to obtain bis (Nε-lauroyl-L-lysine-2-ethylhexyl) oxalylamide).
IR measurement result (KBr): 3293, 1736, 1646, 1552 cm −1
〔製造例３〕 ビス（Ｎε-ラウロイル-Ｌ-リジン−３，５，５−トリメチルヘキシルエステル）オギザリルアミドの合成
製造例２とほぼ同様な方法で合成することができる。
ＩＲ測定結果（ＫＢｒ）：３３１９、３２７８、１７４１、１６６２、１６４２、１５３８ｃｍ-1
[Production Example 3] Synthesis of bis (Nε-lauroyl-L-lysine-3,5,5-trimethylhexyl ester) oxalyl amide can be synthesized in substantially the same manner as in Production Example 2.
IR measurement result (KBr): 3319, 3278, 1741, 1662, 1642, 1538 cm −1
〔製造例４〕 ビス（Ｎε-ラウロイル-Ｌ-リジン）グルタリルアミドナトリウム塩の合成
製造例１とほぼ同様な方法で合成したビス（Ｎε-ラウロイル-Ｌ-リジン）グルタリルアミド 10 mmolを300mlのメタノールに溶解し、１MのNaOH水溶液10mlを加えた。その溶液を蒸発乾固して得られた白色固体をメタノール−エーテルから再結晶して目的物を得た。
ＩＲ測定結果（ＫＢｒ）：３３０７、１７１６、１６４５、１５４９ｃｍ-1
[Production Example 4] Synthesis of bis (Nε-lauroyl-L-lysine) glutarylamide sodium salt 10 ml of bis (Nε-lauroyl-L-lysine) glutarylamide synthesized in the same manner as in Production Example 1 in 300 ml of methanol And 10 ml of 1M NaOH aqueous solution was added. The white solid obtained by evaporating the solution to dryness was recrystallized from methanol-ether to obtain the desired product.
IR measurement result (KBr): 3307, 1716, 1645, 1549 cm −1
〔製造例５〕 ビス（Ｎε-ラウロイル-Ｌ-リジン）アゼラオイルアミドナトリウム塩の合成
製造例４とほぼ同様な方法で合成することができる。
ＩＲ測定結果（ＫＢｒ）：３３０７、１７１５、１６４２、１５５０ｃｍ-1
[Production Example 5] Synthesis of bis (Nε-lauroyl-L-lysine) azelaoylamide sodium salt The compound can be synthesized in the same manner as in Production Example 4.
IR measurement result (KBr): 3307, 1715, 1642, 1550 cm −1
試験方法１
本発明の化合物（製造例１〜３）をふたつき試験管に精秤して加え、各種液状有機媒体を１ｍｌ入れ、蓋をして完全に均一に溶解するまで加熱した。溶解後、２５℃の恒温槽に２時間静置し、様子を肉眼で観察した。ゲル化が不完全な場合は化合物を追加し、完全にゲル化していた場合は液状有機媒体を追加し、１ｍｌ当たりの各液状有機媒体をゲル化させるのに必要な化合物の最低量（ｍｇ）を求めた。ただし加える化合物の最大量は液状有機媒体２ｍｌに対し２００ｍｇまでとし、この状態で液状のものおよび結晶化して析出するものは「ゲル化せず」と評価した。
Test method 1
The compound of the present invention (Production Examples 1 to 3) was precisely weighed and added to a test tube with a lid, 1 ml of various liquid organic media was added, and the mixture was covered and heated until completely dissolved. After dissolution, it was left in a thermostatic bath at 25 ° C. for 2 hours, and the state was observed with the naked eye. Add compounds if gelation is incomplete, add liquid organic media if completely gelled, minimum amount of compound (mg) required to gel each liquid organic media per ml Asked. However, the maximum amount of the compound to be added was up to 200 mg with respect to 2 ml of the liquid organic medium, and in this state, the liquid and those that crystallized and precipitated were evaluated as “not gelled”.
評価
各種液状有機媒体１ｍｌをゲル化させるのに必要な各種ゲル化剤量が２５ｍｇ以下の場合は◎、２６〜３５ｍｇの場合は○、３６〜４５ｍｇの場合は△、４６ｍｇ以上の場合は×とした。
Evaluation ◎ when the amount of various gelling agents required for gelling 1 ml of various liquid organic media is 25 mg or less, ○ for 26 to 35 mg, Δ for 36 to 45 mg, × for 46 mg or more did.
表１より本発明の塩基性アミノ酸誘導体は、従来のゲル化剤に比べ少量の添加で多種の液状有機媒体をゲル化させることが可能であることが明らかである。 From Table 1, it is clear that the basic amino acid derivative of the present invention can gel various liquid organic media with a small amount of addition as compared with conventional gelling agents.
試験法２
本発明の化合物（製造例４、５）につき、液状有機媒体に加え表２に示す各種の液状水媒体についても評価した他は試験方法１と同様に操作し、評価を行った。
Test method 2
The compounds of the present invention (Production Examples 4 and 5) were evaluated in the same manner as in Test Method 1, except that various liquid aqueous media shown in Table 2 were evaluated in addition to the liquid organic medium.
表２より本発明の塩基性アミノ酸誘導体は、多種の液状有機媒体のみならず液状水媒体をもゲル化させられることが明らかとなった。 From Table 2, it became clear that the basic amino acid derivative of the present invention can gel not only various liquid organic media but also liquid aqueous media.
製剤例１：発汗抑制ゲルスティックの製造 Formulation Example 1: Production of antiperspirant gel stick
上記１）〜５）を１３０℃で溶解した後、上記６）を添加して、攪拌しながら放冷し、発汗抑制ゲルスティックを得た。本品は、十分な強度を有するものであった。 After the above 1) to 5) were dissolved at 130 ° C., the above 6) was added and allowed to cool with stirring to obtain a sweating suppression gel stick. This product had sufficient strength.
Claims (8)
Ｒ1、Ｒ2は、各々独立で炭素原子数が５〜２１の直鎖もしくは分岐鎖のアルキル基またはアルケニル基であり、
Ｒ3、Ｒ4は、各々独立で炭素原子数が１〜２２のアルキル基もしくはアルケニル基、水素原子、アルカリ金属、またはアルカリ土類金属であり、前記アルキル基またはアルケニル基は、直鎖でもよく、分岐鎖を有していてもよく、環構造を有していてもよく、
ｚは０以上の整数であり、
ｘ、ｙは２〜４の整数である。） A basic amino acid derivative represented by the following general formula (1).
R 1 and R 2 are each independently a linear or branched alkyl or alkenyl group having 5 to 21 carbon atoms,
R 3 and R 4 are each independently an alkyl group or alkenyl group having 1 to 22 carbon atoms, a hydrogen atom, an alkali metal, or an alkaline earth metal, and the alkyl group or alkenyl group may be linear. , May have a branched chain, may have a ring structure,
z is an integer greater than or equal to 0,
x and y are integers of 2 to 4. )
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| JP6558371B2 (en) * | 2014-07-30 | 2019-08-14 | 味の素株式会社 | Medium chain acyl basic amino acid derivatives |
| CN107108466A (en) | 2014-10-07 | 2017-08-29 | 味之素株式会社 | Containing double（N ε lauroyl lysines）The aqueous solution and its manufacture method of dicarboxylic acid diamide and/or its salt |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5433798B2 (en) * | 1976-09-01 | 1979-10-23 | ||
| JPS56103146A (en) * | 1979-12-28 | 1981-08-18 | Ajinomoto Co Inc | Lysine derivative |
| JPH10245396A (en) * | 1997-03-05 | 1998-09-14 | Pola Chem Ind Inc | Composition containing alkylamide derivative of oligopeptide |
| JP2000256303A (en) * | 1999-03-11 | 2000-09-19 | Ajinomoto Co Inc | Gelling agent for solidifying agent for liquid organic medium |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1485694A (en) * | 1975-01-22 | 1977-09-14 | Ajinomoto Kk | Gelling agents |
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2004
- 2004-02-04 JP JP2004027873A patent/JP4543692B2/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5433798B2 (en) * | 1976-09-01 | 1979-10-23 | ||
| JPS56103146A (en) * | 1979-12-28 | 1981-08-18 | Ajinomoto Co Inc | Lysine derivative |
| JPH10245396A (en) * | 1997-03-05 | 1998-09-14 | Pola Chem Ind Inc | Composition containing alkylamide derivative of oligopeptide |
| JP2000256303A (en) * | 1999-03-11 | 2000-09-19 | Ajinomoto Co Inc | Gelling agent for solidifying agent for liquid organic medium |
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| JP2004323505A (en) | 2004-11-18 |
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