JP3126482B2 - Humectant and method for producing the same - Google Patents
Humectant and method for producing the sameInfo
- Publication number
- JP3126482B2 JP3126482B2 JP04106179A JP10617992A JP3126482B2 JP 3126482 B2 JP3126482 B2 JP 3126482B2 JP 04106179 A JP04106179 A JP 04106179A JP 10617992 A JP10617992 A JP 10617992A JP 3126482 B2 JP3126482 B2 JP 3126482B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxymethyl
- mol
- humectant
- chitin
- chitosan
- 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
- 239000003906 humectant Substances 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 50
- 229920001661 Chitosan Polymers 0.000 claims description 28
- 229920002101 Chitin Polymers 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 230000000850 deacetylating effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000003020 moisturizing effect Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 5
- 229920002674 hyaluronan Polymers 0.000 description 5
- 229960003160 hyaluronic acid Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 carboxypropanoyl Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、Ｎ−（３−カルボキシ
プロパノイル）−６−Ｏ−（カルボキシメチル）キトサ
ンを含む組成物からなる保湿剤及びその製造方法に関す
るものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a humectant comprising a composition containing N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan and a method for producing the same.
【０００２】[0002]
【従来技術及びその問題点】保湿性能を有する化合物と
して、Ｎ−（３−カルボキシプロパノイル）−６−Ｏ−
（カルボキシメチル）キトサンが提案されている（特開
平２−１０５８０１号）。このものは、安価であるとい
う利点を有し、また、ヒアルロン酸と同程度の保湿性能
を有するものの、その保湿性能は未だ不十分で、乾燥下
で使用する化粧水や乳液等に用いる保湿剤としては、不
満足のものである。2. Description of the Related Art N- (3-carboxypropanoyl) -6-O-
(Carboxymethyl) chitosan has been proposed (JP-A-2-105801). This material has the advantage of being inexpensive, although having a moisturizing performance comparable to hyaluronic acid, the moisturizing performance is still insufficient, lotion or used in emulsion or the like humectants for use in drying under Is unsatisfactory.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、Ｎ−（３−
カルボキシプロパノイル）−６−Ｏ−（カルボキシメチ
ル）キトサンを含む保湿性能の改善された保湿剤及びそ
の製造方法を提供することをその課題とする。SUMMARY OF THE INVENTION The present invention relates to N- (3-
An object of the present invention is to provide a humectant containing (carboxypropanoyl) -6-O- (carboxymethyl) chitosan having improved moisturizing performance and a method for producing the same.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、前記課題
を解決すべく鋭意研究を重ねた結果、本発明を完成する
に至った。即ち、本発明によれば、Ｎ−（３−カルボキ
シプロパノイル）−６−Ｏ−（カルボキシメチル）キト
サン４０〜６５モル％、６−Ｏ−（カルボキシメチル）
キトサン５〜２０モル％及び６−Ｏ−（カルボキシメチ
ル）キチン２５〜５０モル％の組成物からなる保湿剤が
提供される。また、本発明によれば、６−Ｏ−（カルボ
キシメチル）キチンをアルカリ溶液中で反応させて、該
キチンの一部を脱アセチル化して６−Ｏ−（カルボキシ
メチル）キトサン５０〜７５モル％と６−Ｏ−（カルボ
キシメチル）キチン５０〜２５モル％の組成物を得る工
程と、該組成物にサクシノイル化剤を反応させて、Ｎ−
（３−カルボキシプロパノイル）−６−Ｏ−（カルボキ
シメチル）キトサン４０〜６５モル％、６−Ｏ−（カル
ボキシメチル）キトサン５〜２０モル％及び６−Ｏ−
（カルボキシメチル）キチン２５〜５０モル％の組成物
を得る工程からなる保湿剤の製造方法が提供される。Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have completed the present invention. That is, according to the present invention, 40-65 mol% of N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan, 6-O- (carboxymethyl)
There is provided a humectant comprising a composition of 5 to 20 mol% of chitosan and 25 to 50 mol% of 6-O- (carboxymethyl) chitin. According to the present invention, 6-O- (carboxymethyl) chitin is reacted in an alkaline solution to deacetylate a part of the chitin to form 50-75 mol% of 6-O- (carboxymethyl) chitosan. To obtain a composition of 50 to 25 mol% of 6-O- (carboxymethyl) chitin, and reacting the composition with a succinoylating agent to give N-
40-65 mol% of (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan, 5-20 mol% of 6-O- (carboxymethyl) chitosan and 6-O-
A method for producing a humectant comprising the step of obtaining a composition of (carboxymethyl) chitin at 25 to 50 mol% is provided.
【０００５】本発明の保湿剤を構成するＮ−（３−カル
ボキシプロパノイル）−６−Ｏ−（カルボキシメチル）
キトサン、６−Ｏ−（カルボキシメチル）キトサン及び
６−Ｏ−（カルボキシメチル）キチンは、それぞれ次の
一般式（１）、一般式（２）及び一般式（３）で表わさ
れる。[0005] N- (3-carboxypropanoyl) -6-O- (carboxymethyl) constituting the humectant of the present invention
Chitosan, 6-O- (carboxymethyl) chitosan and 6-O- (carboxymethyl) chitin are represented by the following general formulas (1), (2) and (3), respectively.
【０００６】[0006]
【化１】 Embedded image
【０００７】[0007]
【化２】 Embedded image
【０００８】[0008]
【化３】 前記式中、Ｍは水素又はアルカリ金属を示し、ｎ、ｍ及
びｐは１０〜５０００の整数を示す。Embedded image In the above formula, M represents hydrogen or an alkali metal, and n, m and p each represent an integer of 10 to 5000.
【０００９】本発明の保湿剤を得るには、６−Ｏ−（カ
ルボキシメチル）キチンを２〜２０ｗｔ％、好ましくは
４〜１２ｗｔ％の苛性ソーダや苛性カリ等のアルカリ性
物質を含むアルカリ溶液中で２０〜１００℃、好ましく
は４０〜８０℃の温度で１〜２４時間、好ましくは３〜
８時間反応させ、そのキチンの一部を脱アセチル化して
６−Ｏ−（カルボキシメチル）キトサン５０〜７５モル
％と６−Ｏ−（カルボキシメチル）キチン２５〜５０モ
ル％からなる組成物を得る。次いで、この組成物に鉱酸
又は有機酸を加えて中和した後、サクシノイル化剤を加
えて、６−Ｏ−（カルボキシメチル）キトサンと反応さ
せて、Ｎ−（３−カルボキシプロパノイル）−６−Ｏ−
（カルボキシメチル）キトサン４０〜６５モル％、６−
Ｏ−（カルボキシメチル）キトサン５〜２０モル％及び
６−Ｏ−（カルボキシメチル）キチン２５〜５０モル％
の組成物を含む反応液を得る。この反応におけるサクシ
ノイル化剤の添加量は、出発原料として用いた６−Ｏ−
（カルボキシメチル）キチンに対して、１〜４倍当量、
好ましくは１〜２倍当量である。反応温度は１０〜７０
℃、好ましくは２０〜６０℃で、反応時間は１〜２４時
間、好ましくは２〜６時間である。サクシノイル化剤と
しては、通常、無水コハク酸が用いられる。前記のよう
にして得られた反応液を透析膜処理するか、あるいはメ
タノールやアセトン等の貧溶媒で沈殿物を析出させて、
付着する塩類を分離することにより本発明の保湿剤を得
る。In order to obtain the humectant of the present invention, 6-O- (carboxymethyl) chitin is dissolved in an alkaline solution containing 2 to 20% by weight, preferably 4 to 12% by weight of an alkaline substance such as caustic soda or potassium hydroxide. 100 ° C., preferably 40 to 80 ° C. for 1 to 24 hours, preferably 3 to
After reacting for 8 hours, a part of the chitin is deacetylated to obtain a composition comprising 50-75 mol% of 6-O- (carboxymethyl) chitosan and 25-50 mol% of 6-O- (carboxymethyl) chitin. . Next, the composition is neutralized by adding a mineral acid or an organic acid, and then a succinoylating agent is added to react with 6-O- (carboxymethyl) chitosan to give N- (3-carboxypropanoyl)-. 6-O-
(Carboxymethyl) chitosan 40-65 mol%, 6-
5-20 mol% of O- (carboxymethyl) chitosan and 25-50 mol% of 6-O- (carboxymethyl) chitin
To obtain a reaction solution containing the composition of The amount of the succinoylating agent added in this reaction depends on the amount of 6-O-
1-4 equivalents to (carboxymethyl) chitin,
Preferably it is 1-2 equivalents. Reaction temperature is 10 to 70
C., preferably 20 to 60 C., and the reaction time is 1 to 24 hours, preferably 2 to 6 hours. As the succinoylating agent, succinic anhydride is usually used. The reaction solution obtained as described above is treated with a dialysis membrane, or a precipitate is precipitated with a poor solvent such as methanol or acetone,
The humectant of the present invention is obtained by separating the attached salts.
【００１０】本発明の保湿剤は、前記したように、Ｎ−
（−３−カルボキシプロパノイル）−６−Ｏ−（カルボ
キシメチル）キトサン４０〜６５モル％、好ましくは４
５〜６０モル％、６−Ｏ−（カルボキシメチル）キトサ
ン５〜２０モル％、好ましくは１０〜１５モル％及び６
−Ｏ−（カルボキシメチル）キチン２５〜５０モル％、
好ましくは３０〜４５モル％からなる。このような成分
組成にすることにより、従来のＮ−（３−カルボキシプ
ロパノイル）−６−Ｏ−（カルボキシメチル）キトサン
からなる保湿剤よりも高い保湿性能を有する保湿剤を得
ることができる。さらに、本発明においては、前記した
６−Ｏ−（カルボキシメチル）キチンの脱アセチル化工
程と、この工程で得られた反応物にサクシノイル化剤を
反応させる工程からなる一連の反応工程を経由して得ら
れた保湿剤の使用が好ましい。本発明の保湿剤を構成す
る各成分を単に混合して形成した保湿剤はｐＨ３〜８で
は白濁を生じ、その安定性に問題が残り、中性〜弱酸性
の用途には不向きである。これに対し、前記一連の工程
を経由して得られた保湿剤ではこのような問題は解消さ
れる。[0010] As described above, the humectant of the present invention comprises N-
(-3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan 40-65 mol%, preferably 4 mol%
5 to 60 mol%, 5 to 20 mol% of 6-O- (carboxymethyl) chitosan, preferably 10 to 15 mol% and 6
-O- (carboxymethyl) chitin 25 to 50 mol%,
Preferably, it consists of 30 to 45 mol%. With such a component composition, it is possible to obtain a humectant having higher moisturizing performance than the conventional humectant composed of N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan. Further, in the present invention, a series of reaction steps including the above-described step of deacetylating 6-O- (carboxymethyl) chitin and the step of reacting the reaction product obtained in this step with a succinoylating agent are performed. It is preferable to use the humectant obtained. The humectant formed by simply mixing the components constituting the humectant of the present invention causes cloudiness at pH 3 to 8, and has a problem in its stability, and is not suitable for neutral to weakly acidic applications. On the other hand, such a problem is solved by the humectant obtained through the series of steps.
【００１１】[0011]
【発明の効果】本発明の保湿剤は、著しく高められた保
湿性能を有し、その保湿性能は従来のヒアルロン酸より
も大幅にすぐれたものである。本発明の保湿剤は、粉末
又は溶液状で、各種化粧品や、医薬品等の分野において
有利に用いられる。The humectant of the present invention has a remarkably enhanced moisturizing performance, which is much better than conventional hyaluronic acid. The humectant of the present invention is in the form of a powder or a solution, and is advantageously used in the fields of various cosmetics and pharmaceuticals.
【００１２】[0012]
【実施例】次に本発明を実施例によりさらに詳細に説明
する。 実施例１ ６−Ｏ−（カルボキシメチル）キチン１４０ｇを６ｗｔ
％ＮａＯＨ４０００ｇに溶解し、７０℃にて６時間かく
はん下で脱アセチル化反応させる。冷却後、酢酸にてＰ
Ｈを６．５に調整し、無水コハク酸７４ｇ（１．５倍当
量）を添加し５０℃にて２時間かくはん下で反応させ
る。１０リットルのメタノールを反応液に添加し、粗製
Ｎ−（３−カルボキシプロパノイル）−６−Ｏ−（カル
ボキシメチル）キトサン（１）、６−Ｏ−（カルボキシ
メチル）キトサン（２）、６−Ｏ−（カルボキシメチ
ル）キチン（３）からなる組成物をえた。これをさらに
メタノールで洗浄し、付着塩類を分離後、乾燥器にて乾
燥し、白色の精製された成分(１)、(２)、(３)の組成物
からなる保湿剤組成物１２０ｇを得た。このときの成分
(１)、(２)及び(３)の組成割合(モル割合)はそれぞれ５
３％、１２％、３５％であった。Next, the present invention will be described in more detail with reference to examples. Example 1 140 g of 6-O- (carboxymethyl) chitin was 6 wt.
The solution is dissolved in 4000 g of NaOH and deacetylated under stirring at 70 ° C. for 6 hours. After cooling, add P
H was adjusted to 6.5, 74 g (1.5 equivalents) of succinic anhydride was added, and the mixture was reacted at 50 ° C. with stirring for 2 hours. 10 liters of methanol was added to the reaction solution and crude N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan (1), 6-O- (carboxymethyl) chitosan (2), 6- A composition comprising O- (carboxymethyl) chitin (3) was obtained. This was further washed with methanol, and the attached salts were separated and dried in a drier to obtain 120 g of a humectant composition composed of white purified components (1), (2) and (3). Was. Components at this time
The composition ratio (molar ratio) of (1), (2) and (3) is 5
They were 3%, 12% and 35%.
【００１３】比較例１ ６−Ｏ−（カルボキシメチル）キチン１４０ｇを２０ｗ
ｔ％％ＮａＯＨ４０００ｇに溶解し、１００℃にて６時
間かくはん下で反応を行う以外は実施例１と同様に操作
する。茶褐色の成分(１)、(２)、(３)からなる組成物１
００ｇを得た。このときの成分(１)、(２)及び(３)の組
成割合（モル割合）はそれぞれ６７％、１８％、１５％
であった。 比較例２ 無水コハク酸２５０ｇ（５倍当量）を添加する以外は実
施例１と同様に操作する。白色の精製された成分(１)、
(２)、(３)からなる保湿剤組成物１２０ｇを得た。この
ときの成分(１)、(２)及び(３)の組成割合（モル割合）
はそれぞれ５９％、４％、３７％であった。 比較例３ ６−Ｏ−（カルボキシメチル）キチン１４０ｇを６ｗｔ
％ＮａＯＨ４０００ｇに溶解し、７０℃にて６時間かく
はん下で反応させる。冷却後、酢酸にてＰＨを６．５に
調整した後、メタノールを加えて沈殿物を析出させ、さ
らにメタノール洗浄により付着塩類の除去を行なった以
外は実施例１と同様に操作する。無水コハク酸を添加し
た時点でゲルが生成してサクシノイル化反応が阻害され
た。白色の精製された成分(１)、(２)、(３)の混合物１
００ｇを得たが、このときの成分(１)、(２)及び(３)の
組成割合（モル割合）はそれぞれ１６％、４７％、３７
％であった。 実施例２ 本発明の組成割合になるように、Ｎ−（３−カルボキシ
プロパノイル）−６−Ｏ−（カルボキシメチル）キトサ
ン、６−Ｏ−（カルボキシメチル）キトサン及び６−Ｏ
−（カルボキシメチル）キチンをそれぞれ混合した。こ
のときの成分(１)、(２)及び(３)の組成割合（モル割
合）はそれぞれ５２％、１５％、３３％であった。この
混合物はｐＨ２の酸性溶液には均一に溶解したが、水中
に溶解させたところ、白濁を生じた。Comparative Example 1 140 g of 6-O- (carboxymethyl) chitin was added to 20 w
The same operation as in Example 1 is carried out except that the reaction mixture is dissolved in 4000 g of t %% NaOH and stirred at 100 ° C. for 6 hours. Composition 1 consisting of brown components (1), (2) and (3)
00 g were obtained. At this time, the composition ratio (molar ratio) of the components (1), (2) and (3) was 67%, 18% and 15%, respectively.
Met. Comparative Example 2 The same operation as in Example 1 was carried out except that 250 g (5 equivalents) of succinic anhydride was added. White purified component (1),
120 g of the humectant composition comprising (2) and (3) was obtained. At this time, the composition ratio (molar ratio) of the components (1), (2) and (3)
Were 59%, 4% and 37%, respectively. Comparative Example 3 6 g of 6 g of 6-O- (carboxymethyl) chitin
The reaction is carried out at 70 ° C. for 6 hours under stirring. After cooling, the pH was adjusted to 6.5 with acetic acid, and methanol was added to precipitate a precipitate, and the same operation as in Example 1 was performed except that attached salts were removed by washing with methanol. When succinic anhydride was added, a gel was formed and the succinoylation reaction was inhibited. Mixture 1 of white purified components (1), (2) and (3)
In this case, the composition ratio (molar ratio) of components (1), (2) and (3) was 16%, 47% and 37%, respectively.
%Met. Example 2 N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan, 6-O- (carboxymethyl) chitosan and 6-O
-(Carboxymethyl) chitin was mixed respectively. At this time, the composition ratio (molar ratio) of components (1), (2) and (3) was 52%, 15% and 33%, respectively. This mixture was uniformly dissolved in the acidic solution of pH 2, but when dissolved in water, it became cloudy.
【００１４】次に、前記のようにして得た各保湿剤につ
いて、以下のようにしてその保湿性能を評価した。 （保湿性試験）２×２ｃｍに切り取ったろ紙に０．１ｗ
ｔ％の各保湿剤水溶液を１０マイクロリットル浸透さ
せ、重量変化を毎分８分まで測定し、３〜８分までの経
時的な重さの変化を対数グラフにプロットする。直線を
引き、その傾きより、水分蒸発速度を相関性で算出し、
保湿性として評価した。その結果を表１に示す。比較の
ため６−Ｏ−（カルボキシメチル）キチン（ＣＭ−キチ
ン）、ヒアルロン酸及び水の水分蒸発始度測定結果を表
１に示す。なお、表１に示す成分(１)、成分(２)及び成
分(３)の内容は次の通りである。 成分(１)：Ｎ−（３−カルボキシプロパノイル）−６−
Ｏ−（カルボキシメチル）キトサン 成分(２)：６−Ｏ−（カルボキシメチル）キトサン 成分(３)：６−Ｏ−（カルボキシメチル）キチンNext, the moisturizing performance of each humectant obtained as described above was evaluated as follows. (Moisturizing test) 0.1w on filter paper cut to 2 × 2cm
Ten microliters of each aqueous solution of the humectant is permeated with t%, the change in weight is measured up to 8 minutes per minute, and the change in weight over time from 3 to 8 minutes is plotted on a logarithmic graph. Draw a straight line, calculate the water evaporation rate by correlation from the slope,
It was evaluated as moisturizing property. Table 1 shows the results. For comparison, Table 1 shows the results of the measurement of the onset of water evaporation of 6-O- (carboxymethyl) chitin (CM-chitin), hyaluronic acid and water. The contents of the components (1), (2) and (3) shown in Table 1 are as follows. Component (1): N- (3-carboxypropanoyl) -6
O- (carboxymethyl) chitosan Component (2): 6-O- (carboxymethyl) chitosan Component (3): 6-O- (carboxymethyl) chitin
【００１５】[0015]
【表１】 [Table 1]
【００１６】表１に示した結果からわかるように、本発
明の保湿剤は従来のヒアルロン酸に比べてその保湿力は
大幅にすぐれている。また、本発明の組成割合からはず
れた組成割合の比較例１、比較例２、比較例３のうち比
較例１、比較例２はヒアルロン酸並の保湿力にとどま
り、比較例３は大幅に保湿力が劣った。As can be seen from the results shown in Table 1, the humectant of the present invention has much better moisturizing power than the conventional hyaluronic acid. In Comparative Examples 1, 2 and 3 having composition ratios deviating from the composition ratios of the present invention, Comparative Examples 1 and 2 have the same moisturizing power as hyaluronic acid, and Comparative Example 3 has a significant moisturizing effect. Power was poor.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ Ｃ０９Ｋ 3/00 Ｃ０９Ｋ 3/00 Ｎ (72)発明者 石川 和裕 北海道登別市千歳町４丁目１番地16号 (72)発明者 境 勝義 北海道登別市千歳町４丁目３番地 (72)発明者 長島 徹哉 埼玉県入間郡越生町大字越生699番地 (56)参考文献 特開 平２−107601（ＪＰ，Ａ) 特開 平２−105801（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) A61K 7/00 - 7/50 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. 7 Identification code FI C09K 3/00 C09K 3/00 N (72) Inventor Kazuhiro Ishikawa 4-1-1, Chitose-cho, Noboribetsu-shi, Hokkaido (72) Inventor Katsuyoshi Sakai 4-3 Chitose-cho, Noboribetsu-shi, Hokkaido (72) Inventor Tetsuya Nagashima 699, Ogose, Oji-cho, Iruma-gun, Saitama (56) References JP-A-2-107601 (JP, A) JP-A-2-105801 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) A61K 7/ 00-7/50 CA (STN) REGISTRY (STN)
Claims (3)
６−Ｏ−（カルボキシメチル）キトサン４０〜６５モル
％、６−Ｏ−（カルボキシメチル）キトサン５〜２０モ
ル％及び６−Ｏ−（カルボキシメチル）キチン２５〜５
０モル％の組成物からなる保湿剤。1. N- (3-carboxypropanoyl)-
40-65 mol% of 6-O- (carboxymethyl) chitosan, 5-20 mol% of 6-O- (carboxymethyl) chitosan and 25-5 mol of 6-O- (carboxymethyl) chitin
A humectant consisting of 0 mol% of the composition.
ル）キチンの一部を脱アセチル化する工程と、該脱アセ
チル化物をサクシノイル化反応させる工程を経由して得
られるものである請求項１の保湿剤。2. The method according to claim 1, wherein the humectant is obtained through a step of deacetylating a part of 6-O- (carboxymethyl) chitin and a step of subjecting the deacetylated product to a succinoylation reaction. Item 5. The humectant of Item 1.
アルカリ溶液中で反応させて、該キチンの一部を脱アセ
チル化して６−Ｏ−（カルボキシメチル）キトサン５０
〜７５モル％と６−Ｏ−（カルボキシメチル）キチン５
０〜２５モル％の組成物を得る工程と、該組成物にサク
シノイル化剤を反応させて、Ｎ−（３−カルボキシプロ
パノイル）−６−Ｏ−（カルボキシメチル）キトサン４
０〜６５モル％、６−Ｏ−（カルボキシメチル）キトサ
ン５〜２０モル％及び６−Ｏ−（カルボキシメチル）キ
チン２５〜５０モル％の組成物を得る工程からなる保湿
剤の製造方法。3. A reaction of 6-O- (carboxymethyl) chitin in an alkaline solution to deacetylate a part of the chitin to form 6-O- (carboxymethyl) chitosan.
~ 75 mol% and 6-O- (carboxymethyl) chitin 5
Obtaining a composition of 0 to 25 mol%, and reacting the composition with a succinoylating agent to give N- (3-carboxypropanoyl) -6-O- (carboxymethyl) chitosan 4
A method for producing a humectant, comprising the step of obtaining a composition of 0 to 65 mol%, 5 to 20 mol% of 6-O- (carboxymethyl) chitosan and 25 to 50 mol% of 6-O- (carboxymethyl) chitin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04106179A JP3126482B2 (en) | 1992-03-31 | 1992-03-31 | Humectant and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04106179A JP3126482B2 (en) | 1992-03-31 | 1992-03-31 | Humectant and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05279239A JPH05279239A (en) | 1993-10-26 |
| JP3126482B2 true JP3126482B2 (en) | 2001-01-22 |
Family
ID=14427016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04106179A Expired - Lifetime JP3126482B2 (en) | 1992-03-31 | 1992-03-31 | Humectant and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3126482B2 (en) |
-
1992
- 1992-03-31 JP JP04106179A patent/JP3126482B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05279239A (en) | 1993-10-26 |
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