JPH05294905A - New carbobetaine and its production - Google Patents
New carbobetaine and its productionInfo
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- JPH05294905A JPH05294905A JP10122892A JP10122892A JPH05294905A JP H05294905 A JPH05294905 A JP H05294905A JP 10122892 A JP10122892 A JP 10122892A JP 10122892 A JP10122892 A JP 10122892A JP H05294905 A JPH05294905 A JP H05294905A
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- carbobetaine
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、毛髪、皮膚化粧料等の
基剤や保湿剤等として有用な新規なベタイン化合物に関
する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel betaine compound useful as a base or moisturizer for hair, skin cosmetics and the like.
【０００２】[0002]
【従来の技術】従来から毛髪や皮膚にしっとりとした感
触を付与する目的で、シャンプー、リンス、洗顔料及び
各種化粧品等に保湿剤を配合することが行われている。
これまでに保湿剤としてはプロピレングリコール、グリ
セリン、尿素、ソルビトール、アルコールのアルキレン
オキサイド付加物等が用いられてきた。しかしながら、
これらのものは保湿性、吸湿性、吸湿速度等で必ずしも
満足のゆくものはなく、またべたつく等の感触の面でも
満足し得るものではなかった。2. Description of the Related Art Conventionally, a moisturizer has been incorporated into shampoos, rinses, face wash and various cosmetics for the purpose of imparting a moist feel to hair and skin.
So far, propylene glycol, glycerin, urea, sorbitol, alkylene oxide adducts of alcohol, etc. have been used as moisturizers. However,
These materials are not always satisfactory in terms of moisture retention, hygroscopicity, moisture absorption rate, etc., and they are not satisfactory in terms of feeling such as stickiness.
【０００３】一方、ヒアルロン酸等の天然多糖成分は、
保湿性能や感触の点では、上記のものより比較的優れて
いる。しかし、天然多糖成分は高価であるため、その使
用範囲は比較的高価な化粧品に限定されてしまうという
欠点があった。On the other hand, natural polysaccharide components such as hyaluronic acid are
It is relatively superior to the above in terms of moisturizing performance and feel. However, since the natural polysaccharide component is expensive, its use range is limited to relatively expensive cosmetics.
【０００４】[0004]
【発明が解決しようとする課題】従って、本発明の目的
は、保湿性に優れ、感触も良好でしかも安価に製造する
ことができる化合物を提供することにある。SUMMARY OF THE INVENTION It is, therefore, an object of the present invention to provide a compound which is excellent in moisturizing property, good in touch and can be produced at low cost.
【０００５】[0005]
【課題を解決するための手段】斯かる実状に鑑み、本発
明者らは鋭意研究を行った結果、下記一般式（１）で表
わされる化合物が保湿性に優れ、しかも安価に製造で
き、毛髪、皮膚化粧料等の基剤、保湿剤等として有用で
あることを見出し、本発明を完成した。In view of such circumstances, as a result of intensive studies by the present inventors, the compound represented by the following general formula (1) has excellent moisturizing properties and can be produced at low cost, and hair The present invention has been completed by discovering that it is useful as a base for skin cosmetics, a moisturizing agent, and the like.
【０００６】すなわち本発明は、次の一般式（１）That is, the present invention provides the following general formula (1):
【０００７】[0007]
【化４】 [Chemical 4]
【０００８】（式中、Ｚ、Ｒ1 、Ｒ2 、Ａ1 、Ａ2 、ｍ
及びｎは次のものを示す。 Ｚ：グリセリン又はグリセリン縮合物よりｍ＋ｎ個の水
酸基を除いた残基を示す。 Ｒ1 、Ｒ2 ：同一又は異なっていてもよく、水素原子又
はメチル基を示す。 Ａ1 、Ａ2 ：同一又は異なっていてもよく、水酸基を有
してもよい炭素数１〜６の直鎖又は分岐鎖のアルキレン
基を示す。 ｍ、ｎ：ｍは０以上、ｎは１以上の数を示すが、ｍ＋ｎ
はＺの価数と同じである。）で表わされるカルボベタイ
ン及びその製造法を提供するものである。(Wherein Z, R 1 , R 2 , A 1 , A 2 , m
And n are as follows. Z: represents a residue obtained by removing m + n hydroxyl groups from glycerin or a glycerin condensate. R 1 and R 2 : may be the same or different and represent a hydrogen atom or a methyl group. A 1 and A 2 are the same or different, and represent a linear or branched alkylene group having 1 to 6 carbon atoms which may have a hydroxyl group. m, n: m is 0 or more, n is a number of 1 or more, m + n
Is the same as the valence of Z. ) And a method for producing the same.
【０００９】本発明のカルボベタインは前記一般式
（１）で表わされるものであり、式中Ｚは、グリセリン
又はグリセリン縮合物よりｍ＋ｎ個の水酸基を除いた残
基を示すが、このグリセリン縮合物としては、グリセリ
ンをアルカリ触媒存在下に、連鎖状、直鎖状又は分岐鎖
状に縮合させたもの、例えばジグリセリン、トリグリセ
リン、テトラグリセリン、ペンタグリセリン、ヘキサグ
リセリン、ヘプタグリセリン、オクタグリセリン、ノナ
グリセリン、デカグリセリン、ドデカグリセリン、テト
ラデカグリセリン、ヘキサデカグリセリン、オクタデカ
グリセリン等の平均縮合度が２０以下のポリグリセリン
が好ましく、特に縮合度１０以下のものが好ましい例と
して挙げられる。また、Ｚで示される基としては、グリ
セリン又はジグリセリンより１個の水酸基を除いたもの
が特に好ましい。The carbobetaine of the present invention is represented by the above-mentioned general formula (1), in which Z represents a residue obtained by removing m + n hydroxyl groups from glycerin or a glycerin condensate. As, in the presence of an alkali catalyst, glycerin, chain, linear or branched condensed, such as diglycerin, triglycerin, tetraglycerin, pentaglycerin, hexaglycerin, heptaglycerin, octaglycerin, nona Polyglycerin having an average condensation degree of 20 or less, such as glycerin, decaglycerin, dodecaglycerin, tetradecaglycerin, hexadecaglycerin, and octadecaglycerin is preferable, and a condensation degree of 10 or less is particularly preferable. As the group represented by Z, one obtained by removing one hydroxyl group from glycerin or diglycerin is particularly preferable.
【００１０】一般式（１）におけるＡ1 、Ａ2 で表わさ
れる基は、同一又は異なっていてもよく、炭素数１〜６
の直鎖又は分岐鎖のアルキレン基を示すが、Ａ1 として
は、エチレン基、プロピレン基又は２−ヒドロキシ−
１，３−プロピレン基が特に好ましく、Ａ2 としては、
メチレン基、エチレン基、プロピレン基又はブチレン基
が特に好ましい。The groups represented by A 1 and A 2 in the general formula (1) may be the same or different and have 1 to 6 carbon atoms.
A straight-chain or branched-chain alkylene group is shown, and A 1 is an ethylene group, a propylene group or 2-hydroxy-
A 1,3-propylene group is particularly preferable, and as A 2 ,
A methylene group, an ethylene group, a propylene group or a butylene group is particularly preferable.
【００１１】また、カルボベタイン（１）において、ｎ
が１であり、かつＲ1 及びＲ2 がメチル基であるもの、
又はｍが０であるものが好ましい。In the carbobetaine (1), n
Is 1 and R 1 and R 2 are methyl groups,
Alternatively, those in which m is 0 are preferable.
【００１２】本発明のカルボベタイン（１）は、例えば
次の式に従って製造することができる。The carbobetaine (1) of the present invention can be produced, for example, according to the following formula.
【００１３】[0013]
【化５】 [Chemical 5]
【００１４】（式中、Ｚ、Ａ1 、Ａ2 、Ｒ1 、Ｒ2 、ｍ
及びｎは前記と同じものを示し、Ｘはハロゲン原子を、
Ｍは陽イオンを示す。）すなわち、アミノ化合物（２）
を化合物（３）と反応せしめれば、本発明のベタイン化
合物（１）を得ることができる。(Wherein Z, A 1 , A 2 , R 1 , R 2 and m
And n are the same as above, X is a halogen atom,
M represents a cation. ) That is, the amino compound (2)
The betaine compound (1) of the present invention can be obtained by reacting with the compound (3).
【００１５】この反応において、使用される化合物
（３）の使用量はアミノ化合物（２）のアミノ基の数に
対して、１〜５倍当量、好ましくは１〜２倍当量とする
ことが好ましい。また、本反応は不活性溶媒の存在下に
おいて、２０〜１２０℃、好ましくは４０〜９０℃の温
度範囲で行われる。ここで用いる不活性溶媒としては、
水、メタノール、エタノール、イソプロピルアルコー
ル、ジメチルホルムアミド、ジメチルスルホキシド等の
極性溶媒から選ばれる１種又は２種以上の混合溶媒が用
いられるが、就中、水のみ、又は水と低級アルコールと
の混合溶媒が好ましい。また、式（３）中のＭの陽イオ
ンは特に限定されないが、アルカリ金属イオン、アンモ
ニウムイオン、総炭素数２〜９のアルカノールアンモニ
ウムイオン等が好ましい。In this reaction, the amount of the compound (3) used is 1 to 5 times equivalent, preferably 1 to 2 times equivalent to the number of amino groups of the amino compound (2). .. Further, this reaction is carried out in the presence of an inert solvent, at a temperature range of 20 to 120 ° C, preferably 40 to 90 ° C. As the inert solvent used here,
One or more mixed solvents selected from polar solvents such as water, methanol, ethanol, isopropyl alcohol, dimethylformamide, and dimethylsulfoxide are used. Among them, only water or a mixed solvent of water and a lower alcohol is used. Is preferred. Further, the cation of M in the formula (3) is not particularly limited, but an alkali metal ion, an ammonium ion, an alkanol ammonium ion having a total carbon number of 2 to 9 and the like are preferable.
【００１６】上記の反応により得られた反応物は、本発
明のカルボベタイン（１）の他、未反応のアミノ化合物
（２）や化合物（３）、その他副生成物が存在するの
で、必要により、溶媒分別法、イオン交換クロマトグラ
フィー法や電気透析法等の公知の方法により精製するこ
とができる。The reaction product obtained by the above reaction contains unreacted amino compound (2), compound (3) and other by-products in addition to the carbobetaine (1) of the present invention. It can be purified by a known method such as a solvent fractionation method, an ion exchange chromatography method or an electrodialysis method.
【００１７】また、本発明の原料である化合物（２）
は、例えば次の式に示す公知の方法により製造すること
ができる。Further, the compound (2) which is a raw material of the present invention
Can be produced, for example, by a known method represented by the following formula.
【００１８】[0018]
【化６】 [Chemical 6]
【００１９】（式中、Ｚ、Ｘ、Ｒ1 、Ｒ2 、ｍ及びｎは
前記と同じものを示す。）すなわち、グリセリン又はグ
リセリン縮合物とエピハロヒドリンとを反応させ、グリ
シジルエーテル化された、グリセリン又はグリセリン縮
合物（４）を得、これとアンモニア、メチルアミン又は
ジメチルアミン（５）とを反応せしめれば化合物（２）
が得られる。化合物（４）と化合物（５）との反応は、
化合物（５）／化合物（４）のモル比を１〜２、好まし
くは１〜１．５とし、反応温度を室温〜８０℃として行
うことが好ましい。このとき、反応は無溶媒で行っても
よいが、メタノール、エタノール、イソプロパノール等
の低級アルコール、クロロホルム等の有機溶媒を用いて
もよい。また、反応は無触媒でも進行する。一方、化合
物（３）としては、クロル酢酸ナトリウム、ブロム吉草
酸リチウム等が例示される。なお、グリセリンを出発原
料とした本発明カルボベタイン（１）の製造工程を例示
すると次の様になる。(In the formula, Z, X, R 1 , R 2 , m and n have the same meanings as described above.) That is, glycerin or a glycerin condensate is reacted with epihalohydrin to form a glycidyl etherified glycerin. Alternatively, a glycerin condensate (4) is obtained, and if this is reacted with ammonia, methylamine or dimethylamine (5), the compound (2) is obtained.
Is obtained. The reaction between the compound (4) and the compound (5) is
It is preferable that the molar ratio of compound (5) / compound (4) is 1 to 2, preferably 1 to 1.5, and the reaction temperature is room temperature to 80 ° C. At this time, the reaction may be carried out without a solvent, but a lower alcohol such as methanol, ethanol or isopropanol, or an organic solvent such as chloroform may be used. Further, the reaction proceeds even without a catalyst. On the other hand, examples of the compound (3) include sodium chloroacetate and lithium bromovalerate. The process for producing the carbobetaine (1) of the present invention using glycerin as a starting material is illustrated below.
【００２０】[0020]
【化７】 [Chemical 7]
【００２１】（式中、Ｒ1 及びＲ2 は前記のものを示
す。）(In the formula, R 1 and R 2 are as defined above.)
【００２２】このようにして得られる本発明のカルボベ
タイン（１）は、保湿性に優れ、かつ安価に製造するこ
とができるため、シャンプー、リンス、各種化粧料等に
幅広く用いることができる。The thus-obtained carbobetaine (1) of the present invention has excellent moisturizing properties and can be produced at low cost, and thus can be widely used in shampoos, rinses, various cosmetics and the like.
【００２３】[0023]
【発明の効果】本発明のカルボベタイン（１）は毛髪、
皮膚に対して極めて良好な保湿効果を与えることがで
き、しかも本発明の製造法によれば安価にカルボベタイ
ン（１）を製造することができる。The carbobetaine (1) of the present invention is for hair,
An extremely good moisturizing effect can be given to the skin, and according to the production method of the present invention, carbobetaine (1) can be produced at low cost.
【００２４】[0024]
【実施例】以下に実施例を挙げ、本発明を更に詳細に説
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.
【００２５】実施例１ カルボベタイン（１）の製造：
反応器にジメチルアミン５０重量％水溶液９００ｇ（１
０．２モル）を入れ、室温で２，３−ジヒドロキシプロ
ピル ２，３−エポキシプロピル エーテル１１２６ｇ
（７．６モル）を３時間で滴下した。滴下後、徐々に昇
温し、５０℃で４時間反応させた。反応終了後、減圧下
で残存ジメチルアミン及び水を除去し、粗生成物１４８
２ｇを得た。これに水１０００ｇを加えて溶解し、反応
系を６０℃に保ちながら、クロル酢酸ソーダ１０００ｇ
（８．７モル）を１０００ｇの水に溶解させた溶液を５
時間で滴下した。その後、６０℃で５時間反応させた。
反応終了後、そのまま、イオン交換クロマトグラフィー
（イオン交換樹脂：ＢＩＯＲＡＤ社製 ＡＧ５０１−Ｘ
８）により精製し、減圧下溶媒を留去して、１−カルボ
キシ−Ｎ，Ｎ−ジメチル−Ｎ−（２，６，７−トリヒド
ロキシ−４−オキサヘプチル）メタンアミニウム ハイ
ドロオキサイドインナーサルト１２４１ｇ（収率６５
％）を得た。このものは吸湿性がグリース状無色固体で
あり、ＨＰＬＣ（カラム；島津製作所社製 シマヅゲル
ＳＣＲ−１０１Ｎ，溶離液；水）純度９９％であった。1 H-NMR(D2O)：δ(ppm) （図１） 3.19(一重線,6H,a) 3.30-3.60(複雑な多重線,6H,b+c+d) 3.61-3.71(二重線,2H,g) 3.72-3.83(五重線,1H,e) 3.84-3.93(一重線,2H,h) 4.18-4.35(五重線,1H,f)Example 1 Preparation of Carbobetaine (1):
900 g of a 50 wt% aqueous solution of dimethylamine (1
0.2 mol), and 1,126 g of 2,3-dihydroxypropyl 2,3-epoxypropyl ether at room temperature
(7.6 mol) was added dropwise over 3 hours. After the dropping, the temperature was gradually raised and the reaction was carried out at 50 ° C. for 4 hours. After the reaction was completed, the residual dimethylamine and water were removed under reduced pressure to obtain a crude product 148
2 g was obtained. To this, 1000 g of water was added and dissolved, and 1000 g of sodium chloroacetate was added while keeping the reaction system at 60 ° C.
(8.7 mol) was dissolved in 1000 g of water to give a solution of 5
Dropped over time. Then, it was made to react at 60 degreeC for 5 hours.
After completion of the reaction, as it is, ion exchange chromatography (ion exchange resin: manufactured by BIORAD AG501-X).
8) and the solvent was distilled off under reduced pressure to give 1-carboxy-N, N-dimethyl-N- (2,6,7-trihydroxy-4-oxaheptyl) methanaminium hydroxide innersalt 1241 g. (Yield 65
%) Was obtained. This had a hygroscopic property as a grease-like colorless solid and had an HPLC (column; Shimadzu SCR-101N manufactured by Shimadzu Corporation, eluent: water) purity of 99%. 1 H-NMR (D 2 O): δ (ppm) (Fig. 1) 3.19 (Singlet, 6H, a ) 3.30-3.60 (Complex multiplet, 6H, b + c + d ) 3.61-3.71 (double Line, 2H, g ) 3.72-3.83 (quintet, 1H, e ) 3.84-3.93 (singlet, 2H, h ) 4.18-4.35 (quintet, 1H, f )
【００２６】[0026]
【化８】 [Chemical 8]
【００２７】質量分析（ＦＡＢイオン化法）； M/Z 252(M+H)+ (M=C10H21O6N)Mass spectrometry (FAB ionization method); M / Z 252 (M + H) + (M = C 10 H 21 O 6 N)
【００２８】実施例２ カルボベタイン（１）の製造：
反応器にジメチルアミン５０重量％水溶液２０８ｇ
（２．４モル）を入れ、室温でポリグリセリン（平均縮
合度：４）のエピクロルヒドリン付加物（平均付加モル
数：３モル）２００ｇ（０．４モル）を室温２時間で滴
下した。滴下後、徐々に昇温し、５０℃で６時間反応さ
せた。反応終了後、減圧下で残存ジメチルアミン及び水
を除去し、粗生成物２５３．８ｇを得た。これに水２５
０ｇを加えて溶解し、反応系を６０℃に保ちながら、ク
ロル酢酸ソーダ１９０ｇ（１．６モル）を２００ｇの水
に溶解させた溶液を５時間で滴下した。その後、６０℃
で５時間反応させた。反応終了後、そのままイオン交換
クロマトグラフィー（イオン交換樹脂：ＢＩＯ ＲＡＤ
社製 ＡＧ５０１−Ｘ８）により精製し、目的物である
ポリグリセリン（平均縮合度：４）のカルボキシベタイ
ン化物２０８ｇ（収率６４％）を得た。このものはポリ
グリセリン１モル当り平均３個のカルボキシベタイン基
を有していた。Example 2 Preparation of Carbobetaine (1):
208 g of 50 wt% aqueous dimethylamine solution in the reactor
(2.4 mol) was added, and 200 g (0.4 mol) of an epichlorohydrin adduct of polyglycerin (average condensation degree: 4) (average number of added mols: 3 mol) was added dropwise at room temperature for 2 hours. After the dropping, the temperature was gradually raised and the reaction was carried out at 50 ° C. for 6 hours. After the reaction was completed, the residual dimethylamine and water were removed under reduced pressure to obtain 253.8 g of a crude product. Water on this 25
A solution prepared by dissolving 190 g (1.6 mol) of sodium chloroacetate in 200 g of water was added dropwise over 5 hours while maintaining the reaction system at 60 ° C. After that, 60 ℃
And reacted for 5 hours. After completion of the reaction, ion exchange chromatography (ion exchange resin: BIO RAD
The product was purified by AG501-X8) to obtain 208 g (yield 64%) of a carboxybetaine compound of the target polyglycerol (average condensation degree: 4). This had an average of 3 carboxybetaine groups per mole of polyglycerin.
【００２９】[0029]
【化９】 [Chemical 9]
【００３０】[0030]
【図１】実施例１で得られた本発明のカルボベタイン
（１）の1H-NMRスペクトル図である。1 is a 1 H-NMR spectrum diagram of carbobetaine (1) of the present invention obtained in Example 1. FIG.
【図２】実施例２で得られた本発明のカルボベタイン
（１）の1H-NMRスペクトル図である。FIG. 2 is a 1 H-NMR spectrum diagram of carbobetaine (1) of the present invention obtained in Example 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 Ｃ０７Ｃ 227/18 8930−4Ｈ (72)発明者 今井 一康 東京都板橋区小豆沢２−10−10 (72)発明者 藤倉 芳明 栃木県宇都宮市山本町271−６─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Internal reference number FI Technical indication location C07C 227/18 8930-4H (72) Inventor Kazuyasu Imai 2-10-10 Shozuzawa, Itabashi-ku, Tokyo (72) Inventor Yoshiaki Fujikura 271-6 Yamamotocho, Utsunomiya City, Tochigi Prefecture
Claims (7)
タイン。 【化１】 （式中、Ｚ、Ｒ1 、Ｒ2 、Ａ1 、Ａ2 、ｍ及びｎは次の
ものを示す。 Ｚ：グリセリン又はグリセリン縮合物よりｍ＋ｎ個の水
酸基を除いた残基を示す。 Ｒ1 、Ｒ2 ：同一又は異なっていてもよく、水素原子又
はメチル基を示す。 Ａ1 、Ａ2 ：同一又は異なっていてもよく、水酸基を有
してもよい炭素数１〜６の直鎖又は分岐鎖のアルキレン
基を示す。 ｍ、ｎ：ｍは０以上、ｎは１以上の数を示すが、ｍ＋ｎ
はＺの価数と同じである。）1. Carbobetaine represented by the following general formula (1): [Chemical 1] (In the formula, Z, R 1 , R 2 , A 1 , A 2 , m and n represent the following: Z: a residue obtained by removing m + n hydroxyl groups from glycerin or a glycerin condensate. R 1 , R 2 : may be the same or different and represent a hydrogen atom or a methyl group A 1 , A 2 : may be the same or different and may have a hydroxyl group, and may be a straight chain having 1 to 6 carbon atoms or Represents a branched alkylene group, m, n: m is 0 or more, n is 1 or more, m + n
Is the same as the valence of Z. )
ロキシ−１，３−プロピレン基である請求項１記載のベ
タイン化合物。2. The betaine compound according to claim 1 , wherein in the general formula (1), A 1 is a 2-hydroxy-1,3-propylene group.
１０のポリグリセリンよりｍ＋ｎ個の水酸基を除いた残
基である請求項１又は２記載のカルボベタイン。3. In the general formula (1), Z is a condensation degree of 1 to 1.
Carbobetaine according to claim 1 or 2, which is a residue obtained by removing m + n hydroxyl groups from the polyglycerol of 10.
Ｒ1 及びＲ2 がメチル基である請求項１、２又は３記載
のカルボベタイン。4. In the general formula (1), n is 1,
Carbobetaine according to claim 1, 2 or 3, wherein R 1 and R 2 are methyl groups.
基又はエチレン基である請求項１〜４のいずれかの項記
載のカルボベタイン。5. The carbobetaine according to claim 1, wherein in the general formula (1), A 2 is a methylene group or an ethylene group.
求項１〜５のいずれかの項記載のカルボベタイン。6. The carbobetaine according to claim 1, wherein in the general formula (1), m is 0.
示す。 Ｚ：グリセリン又はグリセリン縮合物よりｍ＋ｎ個の水
酸基を除いた残基を示す。 Ｒ1 、Ｒ2 ：同一又は異なっていてもよく、水素原子又
はメチル基を示す。 Ａ1 ：水酸基を有してもよい炭素数１〜６の直鎖又は分
岐鎖のアルキレン基を示す。 ｍ、ｎ：ｍは０以上、ｎは１以上の数を示すが、ｍ＋ｎ
はＺの価数と同じである。） で表わされるアミノ化合物と次の一般式（３） X-A2-CO2M （３） （式中、Ｘ、Ａ2 及びＭは次のものを示す。 Ｘ：ハロゲン原子を示す。 Ａ2 ：水酸基を有していてもよい炭素数１〜６の直鎖又
は分岐鎖のアルキレン基を示す。 Ｍ：陽イオンを示す。） で表わされる化合物を反応させることを特徴とする次の
一般式（１） 【化３】 （式中、Ｚ、Ｒ1 、Ｒ2 、Ａ1 、Ａ2 、ｍ及びｎは前記
のものを示す。）で表わされるカルボベタインの製造
法。7. The following general formula (2): (In the formula, Z, R 1 , R 2 , A 1 , m and n represent the following: Z: a residue obtained by removing m + n hydroxyl groups from glycerin or a glycerin condensate. R 1 , R 2 : May be the same or different and represent a hydrogen atom or a methyl group A 1 : represent a linear or branched alkylene group having 1 to 6 carbon atoms and optionally having a hydroxyl group, m and n: m are 0 or more, n is a number of 1 or more, m + n
Is the same as the valence of Z. ) And an amino compound represented by the following general formula (3) XA 2 —CO 2 M (3) (wherein X, A 2 and M represent the following: X: represents a halogen atom A 2 : Represents a linear or branched alkylene group having 1 to 6 carbon atoms, which may have a hydroxyl group, M: represents a cation, and is reacted with a compound represented by the following general formula ( 1) [Chemical Formula 3] (In the formula, Z, R 1 , R 2 , A 1 , A 2 , m and n are the same as described above.) A process for producing carbobetaine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04101228A JP3076135B2 (en) | 1992-04-21 | 1992-04-21 | New carbobetaine and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04101228A JP3076135B2 (en) | 1992-04-21 | 1992-04-21 | New carbobetaine and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05294905A true JPH05294905A (en) | 1993-11-09 |
| JP3076135B2 JP3076135B2 (en) | 2000-08-14 |
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ID=14295044
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2755689A1 (en) * | 1996-11-14 | 1998-05-15 | Ceca Sa | PROCESS FOR THE PREPARATION OF POLYGLYCERYL AMINES, THE AMINES OBTAINED AND THEIR DERIVATIVES |
| US6452030B1 (en) | 1999-11-17 | 2002-09-17 | Nippon Shokubai Co., Ltd. | Betaine compound and process for production thereof |
| WO2007101527A1 (en) * | 2006-03-07 | 2007-09-13 | Unilever Plc | Personal care compositions containing quaternary ammonium trihydroxy substituted dipropyl ether |
-
1992
- 1992-04-21 JP JP04101228A patent/JP3076135B2/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2755689A1 (en) * | 1996-11-14 | 1998-05-15 | Ceca Sa | PROCESS FOR THE PREPARATION OF POLYGLYCERYL AMINES, THE AMINES OBTAINED AND THEIR DERIVATIVES |
| EP0842921A1 (en) * | 1996-11-14 | 1998-05-20 | Ceca S.A. | Process for the preparation of polyglycerylated amines, amines so obtained and their derivatives |
| US6452030B1 (en) | 1999-11-17 | 2002-09-17 | Nippon Shokubai Co., Ltd. | Betaine compound and process for production thereof |
| WO2007101527A1 (en) * | 2006-03-07 | 2007-09-13 | Unilever Plc | Personal care compositions containing quaternary ammonium trihydroxy substituted dipropyl ether |
| JP2009529012A (en) * | 2006-03-07 | 2009-08-13 | ユニリーバー・ナームローゼ・ベンノートシヤープ | Personal care composition comprising quaternary ammonium trihydroxy substituted dipropyl ether |
| US7659234B2 (en) | 2006-03-07 | 2010-02-09 | Conopco, Inc. | Personal care compositions containing quaternary ammonium trihydroxy substituted dipropyl ether |
| KR101350094B1 (en) * | 2006-03-07 | 2014-02-14 | 유니레버 엔.브이. | Personal care compositions containing quaternary ammonium trihydroxy substituted dipropyl ether |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3076135B2 (en) | 2000-08-14 |
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