JPH05339301A - Preparation of cellulose carboxylate derivative - Google Patents
Preparation of cellulose carboxylate derivativeInfo
- Publication number
- JPH05339301A JPH05339301A JP4145846A JP14584692A JPH05339301A JP H05339301 A JPH05339301 A JP H05339301A JP 4145846 A JP4145846 A JP 4145846A JP 14584692 A JP14584692 A JP 14584692A JP H05339301 A JPH05339301 A JP H05339301A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- producing
- acid ester
- derivative according
- cellulose derivative
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、固形医薬品の腸溶性コ
ーティング剤、写真フィルムのアンチハレーション用バ
インダなどとして有用なカルボン酸エステル系セルロー
ス誘導体の製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a carboxylic acid ester type cellulose derivative useful as an enteric coating agent for solid pharmaceuticals, a binder for antihalation of photographic films and the like.
【０００２】[0002]
【従来の技術】カルボン酸エステル系セルロース誘導体
は、酸性あるいは中性の水には溶解しない。アルカリ性
の水には溶解する。このためそのようなカルボン酸エス
テル系セルロース誘導体は従来、医薬用腸溶性コーティ
ング剤として錠剤、顆粒剤、丸薬などに用いられてい
る。そのほか、アンチハレーション用バインダとして写
真フィルムなどにも用いられている。2. Description of the Related Art Carboxylic acid ester-based cellulose derivatives are not soluble in acidic or neutral water. It dissolves in alkaline water. Therefore, such a carboxylic acid ester-based cellulose derivative has hitherto been used as a medicinal enteric coating agent in tablets, granules, pills and the like. In addition, it is also used for photographic film as a binder for anti-halation.
【０００３】このようなカルボン酸エステル系セルロー
ス誘導体について、セルロースアセタートであるヘキサ
ヒドロフタル酸エステルが特公昭43−3408号公報に、ヒ
ドロキシアルキルアルキルセルロースのフタル酸エステ
ルが特公昭47−6436号公報、特公昭48-43808号公報に、
セルロースエーテルのテトラヒドロフタル酸エステル及
びヘキサヒドロフタル酸エステルが特公昭46-29743号公
報にそれぞれ開示されている。ヒドロキシアルキルアル
キルキルセルロースの酸性サクシニル及び脂肪族モノア
シル混成エステルが特公昭57-25008号公報に開示されて
いる。Regarding such carboxylic acid ester type cellulose derivatives, hexahydrophthalic acid ester which is a cellulose acetate is disclosed in JP-B-43-3408, and phthalic acid ester of hydroxyalkylalkyl cellulose is disclosed in JP-B-47-6436. , Japanese Patent Publication No. 48-43808,
The tetrahydrophthalic acid ester and the hexahydrophthalic acid ester of cellulose ether are disclosed in JP-B-46-29743. An acidic succinyl and aliphatic monoacyl hybrid ester of hydroxyalkylalkyl-killed cellulose is disclosed in JP-B-57-25008.
【０００４】カルボン酸エステル系セルロース誘導体の
合成には、一般にセルロース類と酸無水物とをエステル
反応させて行う。反応溶媒には酢酸を用い、酢酸ナトリ
ウムなどカルボン酸のアルカリ金属塩を触媒とする。同
じ合成には、出発物質のセルロース類と多価カルボン酸
無水物とをエステル反応させる方法もある。この場合、
反応溶媒にはアセトンあるいはジメチルホルムアミドな
どを用い、反応触媒にはピリジンなどの塩基性触媒が用
いられる。竪型反応機で撹拌して反応させる。The synthesis of a carboxylic acid ester type cellulose derivative is generally carried out by ester reaction of celluloses and acid anhydride. Acetic acid is used as a reaction solvent, and an alkali metal salt of carboxylic acid such as sodium acetate is used as a catalyst. In the same synthesis, there is also a method in which the starting materials celluloses and a polycarboxylic acid anhydride are subjected to an ester reaction. in this case,
Acetone or dimethylformamide is used as the reaction solvent, and a basic catalyst such as pyridine is used as the reaction catalyst. Stir with a vertical reactor to react.
【０００５】[0005]
【発明が解決しようとする課題】セルロース類と酸無水
物との反応効率を高めるには溶質となる出発原料のセル
ロース類の濃度を高くする必要がある。ところがセルロ
ース類の濃度を高めることは容易ではない。セルロース
類は酢酸中で溶液の粘度を高める。そのためセルロース
類を酢酸溶媒中に高濃度で均一に溶解させることは難し
い。セルロース類を均一に溶解するには、いきおい酢酸
溶媒の量を増加しなければならなくなる。こうなると、
セルロース類の濃度が下がって反応効率を上げることは
できなくなる。SUMMARY OF THE INVENTION In order to increase the reaction efficiency between celluloses and acid anhydrides, it is necessary to increase the concentration of the starting celluloses that are solutes. However, it is not easy to increase the concentration of celluloses. Cellulose increases the viscosity of the solution in acetic acid. Therefore, it is difficult to uniformly dissolve the celluloses in the acetic acid solvent at a high concentration. In order to uniformly dissolve the celluloses, the amount of acetic acid solvent must be increased. This happens when,
It becomes impossible to improve the reaction efficiency because the concentration of celluloses is lowered.
【０００６】酢酸に対して溶解性の高いセルロース類は
存在する。これらを使用すればエステル反応の効率は高
くなるが、そのような溶解性の高いセルロース類は分子
量が小さく重合度が小さい。重合度が小さいと高分子物
質としての特性を十分には得られないという問題点があ
る。There exist celluloses that are highly soluble in acetic acid. When these are used, the efficiency of the ester reaction is increased, but such highly soluble celluloses have a small molecular weight and a small degree of polymerization. If the degree of polymerization is small, there is a problem that the characteristics as a polymer substance cannot be sufficiently obtained.
【０００７】本発明は前記の課題を解決するためなされ
たもので、セルロース類と酸無水物とのエステル化反応
の効率を高くすることができるカルボン酸エステル系セ
ルロース誘導体の製造方法を提供することを目的とす
る。The present invention has been made to solve the above problems, and provides a method for producing a carboxylic acid ester-based cellulose derivative capable of increasing the efficiency of the esterification reaction between celluloses and acid anhydrides. With the goal.
【０００８】[0008]
【課題を解決するための手段】前記の目的を達成するた
めになされた本発明のカルボン酸エステル系セルロース
誘導体の製造方法は、酢酸ナトリウムを触媒として酢酸
溶媒中でセルロース類と多価カルボン酸無水物とをエス
テル反応させるに当り、酢酸溶媒の使用量を該セルロー
ス類に対して１〜２倍重量とし、双軸撹拌機で撹拌す
る。The method for producing a carboxylic acid ester-based cellulose derivative of the present invention, which has been made to achieve the above-mentioned object, comprises the steps of using cellulose acetate and polycarboxylic acid anhydride in an acetic acid solvent with sodium acetate as a catalyst. In the ester reaction with the product, the amount of the acetic acid solvent used is 1 to 2 times the weight of the cellulose and the mixture is stirred with a twin-screw stirrer.
【０００９】カルボン酸エステル系セルロース誘導体を
製造するに当って用いられるセルロース類としては、メ
チルセルロースやエチルセルロースなどのアルキルセル
ロースが挙げられる。そのほかにも、ヒドロキシエチル
セルロース、ヒドロキシプロピルセルロース等のヒドロ
キシアルキルセルロースが挙げられ、ヒドロキシエチル
メチルセルロース、ヒドロキシプロピルメチルセルロー
ス等のヒドロキシアルキルアルキルセルロースも挙げら
れる。そのほか、セルロースアセタートなど、Ｏ−アシ
ル基結合を有する低級脂肪酸エステルなども挙げられ
る。Examples of celluloses used in producing the carboxylic acid ester-based cellulose derivative include alkyl celluloses such as methyl cellulose and ethyl cellulose. In addition, hydroxyalkyl cellulose such as hydroxyethyl cellulose and hydroxypropyl cellulose may be mentioned, and hydroxyalkyl alkyl cellulose such as hydroxyethyl methyl cellulose and hydroxypropyl methyl cellulose may also be mentioned. Other examples include lower fatty acid esters having an O-acyl group bond such as cellulose acetate.
【００１０】このようなセルロース類とエステル反応さ
せる多価カルボン酸無水物としては、無水フタル酸、無
水テトラヒドロフタル酸、無水ヘキサヒドロフタル酸、
無水マレイン酸、無水コハク酸、無水トリメリット酸な
どが例示される。これらは単独で使用されてもよく、２
種以上組み合わされてもよい。これらはその反応目的物
に応じて更に無水酢酸のような無水脂肪族モノカルボン
酸の混在している混酸でもよい。混酸でなくてもよい。Examples of polyvalent carboxylic acid anhydrides to be ester-reacted with such celluloses include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride,
Examples include maleic anhydride, succinic anhydride, trimellitic anhydride, and the like. These may be used alone 2
You may combine 2 or more types. These may be mixed acids in which an aliphatic monocarboxylic acid anhydride such as acetic anhydride is further mixed depending on the reaction target. It need not be a mixed acid.
【００１１】反応触媒にはカルボン酸アルカリ金属塩が
好ましい。特に、酢酸ナトリウムが安価で好ましい。反
応溶媒には酢酸を用いる。The reaction catalyst is preferably a carboxylic acid alkali metal salt. In particular, sodium acetate is preferable because it is inexpensive. Acetic acid is used as the reaction solvent.
【００１２】多価カルボン酸無水物の使用量はセルロー
ス類との反応効率、合成目的物のエステル置換度を考慮
して任意に選択すればよい。The amount of the polyvalent carboxylic acid anhydride to be used may be arbitrarily selected in consideration of the reaction efficiency with celluloses and the degree of ester substitution of the synthetic object.
【００１３】触媒の使用量は、酢酸溶媒の仕込量及びセ
ルロース類との反応物である酸無水物の種類あるいは仕
込量により異なる。反応効率、合成目的物のエステル置
換度を考慮して任意に選択すればよい。一般にはおおむ
ね原料セルロース類に対して、０．２〜０．８倍重量が
好ましい。The amount of the catalyst used varies depending on the charged amount of the acetic acid solvent and the type or charged amount of the acid anhydride which is a reaction product with celluloses. It may be arbitrarily selected in consideration of the reaction efficiency and the degree of ester substitution of the target product. Generally, 0.2 to 0.8 times the weight of the raw material cellulose is preferable.
【００１４】酢酸溶媒の使用量は該セルロース類に対し
て１〜２倍重量、好ましくは該セルロース類の１〜１．
５倍重量とするとよい。溶媒の量を等重量より少なくす
ると、粘性が高く撹拌が困難になる。しかも、原料のセ
ルロース類が十分に溶解されないため、得られる反応生
成物のエステル置換率が不均一になって好ましくない。
２倍重量より多いと十分な反応速度が得られず好ましく
ない。The amount of acetic acid solvent used is 1 to 2 times the weight of the cellulose, preferably 1 to 1.
It is recommended that the weight be 5 times. When the amount of the solvent is less than the equal weight, the viscosity is high and stirring becomes difficult. Moreover, since the raw material cellulose is not sufficiently dissolved, the ester substitution rate of the obtained reaction product becomes uneven, which is not preferable.
If the amount is more than twice the weight, a sufficient reaction rate cannot be obtained, which is not preferable.
【００１５】本発明ではこのような反応混合液の中でセ
ルロース類と多価カルボン酸無水物とをエステル反応さ
せる。エステル反応に当っては双軸撹拌機で撹拌する。
双軸撹拌機は高粘性の流体で均一な混合物を形成して化
学反応を行うのに適した装置である。これは加熱融解あ
るいは冷却を行う目的のために使用されており、ニー
ダ、インターナルミキサ等の名称で一般に市販されてい
る。上記のような反応混合液は高粘性体であり、高粘性
体を通常の竪型反応機で撹拌することは困難である。上
記のような双軸撹拌機で撹拌すると高粘性体の均一な反
応が可能となる。In the present invention, the cellulose and the polycarboxylic acid anhydride are subjected to an ester reaction in such a reaction mixture. The ester reaction is agitated with a twin-screw agitator.
A twin-screw stirrer is a suitable device for forming a homogeneous mixture of highly viscous fluids and conducting a chemical reaction. It is used for the purpose of heating and melting or cooling, and is generally commercially available under the names such as kneader and internal mixer. The reaction mixture liquid as described above is a highly viscous substance, and it is difficult to stir the highly viscous substance with an ordinary vertical reactor. Stirring with a twin-screw stirrer as described above enables a uniform reaction of highly viscous substances.
【００１６】セルロース類と多価カルボン酸無水物との
エステル反応は反応器中に触媒と溶媒とセルロース類と
多価カルボン酸無水物とをそれぞれ所定量で一緒に仕込
んで行うとよい。The ester reaction between the cellulose and the polycarboxylic acid anhydride is preferably carried out by charging the catalyst, the solvent, the cellulose and the polycarboxylic acid anhydride together in a predetermined amount in a reactor.
【００１７】反応温度は６０〜１１０℃、反応時間はお
おむね２〜８時間である。反応終結後、反応粗生成物を
含む反応液に多量の水を加えれば生成物を析出させるこ
とができる。The reaction temperature is 60 to 110 ° C., and the reaction time is generally 2 to 8 hours. After the completion of the reaction, the product can be precipitated by adding a large amount of water to the reaction solution containing the reaction crude product.
【００１８】水で十分に洗浄して精製し、乾燥させれば
高純度の目的物、例えば、ヒドロキシプロピルメチルセ
ルロースフタラート、あるいは、ヒドロキシプロピルメ
チルセルロースアセタートサクシナートを得ることがで
きる。If the product is thoroughly washed with water, purified, and dried, a high-purity target product such as hydroxypropylmethylcellulose phthalate or hydroxypropylmethylcellulose acetate succinate can be obtained.
【００１９】[0019]
【発明の効果】本発明のカルボン酸エステル系セルロー
ス誘導体の製造方法によれば、セルロース類と酸無水物
とのエステル化反応の効率を高くすることができ、工業
的にも高速度でカルボン酸エステル系セルロース誘導体
を量産できるようになる。EFFECT OF THE INVENTION According to the method for producing a carboxylic acid ester-based cellulose derivative of the present invention, the efficiency of the esterification reaction between the cellulose and the acid anhydride can be increased, and the carboxylic acid can be industrially produced at a high speed. It becomes possible to mass-produce ester-based cellulose derivatives.
【００２０】[0020]
【実施例】以下、本発明の実施例を説明する。 実施例１〜３ 双軸撹拌機を有する５１ニーダ型反応機にヒドロキシプ
ロピルメチルセルロース４００ｇと、表１に示す量の酢
酸、無水フタル酸、酢酸ナトリウムを仕込み、８５℃で
３時間、ヒドロキシプロピルメチルセルロースと無水フ
タル酸とを反応させた。ヒドロキシプロピルメチルセル
ロースには、グルコース単位１個当りのヒドロキシプロ
ポキシル基置換数０．２４、メトキシル基置換数１．８
７のヒドロキシプロピルメチルセルロースを用いた。EXAMPLES Examples of the present invention will be described below. Examples 1 to 3 400 g of hydroxypropyl methylcellulose, 400 g of acetic acid, phthalic anhydride and sodium acetate shown in Table 1 were charged in a 51 kneader type reactor having a twin-screw stirrer, and hydroxypropyl methylcellulose was added at 85 ° C. for 3 hours. Reacted with phthalic anhydride. Hydroxypropylmethyl cellulose has a hydroxypropoxyl group substitution number of 0.24 and a methoxyl group substitution number of 1.8 per glucose unit.
Hydroxypropyl methylcellulose of 7 was used.
【００２１】次いで、反応液にその約５倍重量の水を徐
々に加えて反応生成物を析出させ、その析出物を十分に
水洗、乾燥した。得られた析出物を分析した結果、生成
物はグルコース１個当りの２−カルボキシ−ベンゾイル
基の置換数がいずれも０．６５のヒドロキシプロピルメ
チルセルロースフタラートだった。酢酸、無水フタル
酸、酢酸ナトリウムの各仕込み量と無水フタル酸の反応
効率を表１に示す。酢酸の仕込量の減少に従い無水フタ
ル酸の反応効率が高くなっていることが分かった。Next, about 5 times its weight of water was gradually added to the reaction solution to precipitate a reaction product, and the precipitate was washed thoroughly with water and dried. As a result of analyzing the obtained precipitate, the product was hydroxypropylmethylcellulose phthalate in which the substitution number of 2-carboxy-benzoyl group per glucose was 0.65. Table 1 shows the charged amounts of acetic acid, phthalic anhydride, and sodium acetate and the reaction efficiency of phthalic anhydride. It was found that the reaction efficiency of phthalic anhydride increased as the charged amount of acetic acid decreased.
【００２２】[0022]
【表１】 [Table 1]
【００２３】比較例１、２ 実施例１と同様に表１に示す量で酢酸・無水フタル酸・
酢酸ナトリウムを仕込み、ヒドロキシプロピルメチルセ
ルロースフタラートを合成した。重量でセルロース類の
２倍以上の酢酸を用いると反応効率が低下することが分
かった。Comparative Examples 1 and 2 As in Example 1, acetic acid / phthalic anhydride /
Sodium acetate was charged to synthesize hydroxypropylmethyl cellulose phthalate. It was found that the reaction efficiency decreases when acetic acid which is more than twice the weight of cellulose is used.
【００２４】実施例４〜６ 無水フタル酸の代りに無水コハク酸と無水酢酸との混酸
を用い、表２に示す量でその混酸とヒドロキシプロピル
メチルセルロースとのエステル反応を行った。グルコー
ス単位１個当りの３−カルボキシ−プロピオニル基置換
数０．３０、アセチル基置換数０．５３のカルボン酸エ
ステル系セルロース誘導体を得た。Examples 4 to 6 A mixed acid of succinic anhydride and acetic anhydride was used in place of phthalic anhydride, and an ester reaction of the mixed acid and hydroxypropylmethylcellulose was carried out in the amounts shown in Table 2. A carboxylic acid ester-based cellulose derivative having a 3-carboxy-propionyl group substitution number of 0.30 and an acetyl group substitution number of 0.53 per glucose unit was obtained.
【００２５】酢酸、無水コハク酸、無水酢酸、酢酸ナト
リウムの仕込量及び、無水フタル酸の反応効率を表１に
示す。酢酸の仕込量が減少するに従って無水コハク酸及
び無水酢酸の反応効率が高くなっていることが分かっ
た。Table 1 shows the charged amounts of acetic acid, succinic anhydride, acetic anhydride and sodium acetate, and the reaction efficiency of phthalic anhydride. It was found that the reaction efficiency of succinic anhydride and acetic anhydride increased as the charged amount of acetic acid decreased.
【００２６】[0026]
【表２】 [Table 2]
【００２７】比較例３、４ 実施例４と同様に表２に示す量の無水コハク酸と無水酢
酸との混酸を用いた。重量でセルロース類の２倍以上の
酢酸を用いると反応効率が低下することが分かった。Comparative Examples 3 and 4 As in Example 4, the amounts of mixed acid of succinic anhydride and acetic anhydride shown in Table 2 were used. It was found that the reaction efficiency decreases when acetic acid which is more than twice the weight of cellulose is used.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 丸山 和政 新潟県中頸城郡頸城村大字西福島28番地の １ 信越化学工業株式会社合成技術研究所 内 (72)発明者 武藤 泰明 新潟県中頸城郡頸城村大字西福島28番地の １ 信越化学工業株式会社合成技術研究所 内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazumasa Maruyama 28, Nishi-Fukushima, Nakakubiki-gun, Nakakubiki-gun, Niigata Prefecture 1 Shinsei Chemical Industry Co., Ltd. Synthetic Technology Laboratory (72) Inventor Yasuaki Mutoh Naka-Kijo, Niigata Prefecture 28, Nishi-Fukushima, Kubiki, Gun-gun 1 Synthetic Technology Laboratory, Shin-Etsu Chemical Co., Ltd.
Claims (18)
酢酸溶媒中でセルロース類と多価カルボン酸無水物とを
エステル反応させるに当り、酢酸溶媒の使用量を該セル
ロース類に対して１〜２倍重量とし、双軸撹拌機で撹拌
することを特徴とするカルボン酸エステル系セルロース
誘導体の製造方法。1. The amount of acetic acid solvent used is 1 to 2 times that of the cellulose in the ester reaction of the cellulose and polycarboxylic acid anhydride in an acetic acid solvent using an alkali metal carboxylic acid as a catalyst. A method for producing a carboxylic acid ester-based cellulose derivative, characterized in that the weight is used and the mixture is stirred with a twin-screw stirrer.
ス、ヒドロキシアルキルセルロース、ヒドロキシアルキ
ルアルキルセルロースの中から選択される請求項１に記
載のカルボン酸エステル系セルロース誘導体の製造方
法。2. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the cellulose is selected from alkyl cellulose, hydroxyalkyl cellulose, and hydroxyalkylalkyl cellulose.
チル基、プロピル基の中から選択される請求項２に記載
のカルボン酸エステル系セルロース誘導体の製造方法。3. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 2, wherein each of the alkyl groups is selected from a methyl group, an ethyl group and a propyl group.
ースがヒドロキシプロピルメチルセルロースである請求
項３に記載のカルボン酸エステル系セルロース誘導体の
製造方法。4. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 3, wherein the hydroxyalkylalkylcellulose is hydroxypropylmethylcellulose.
基結合を有しているセルロース類である請求項１〜４の
いずれかに記載の製造方法。5. The production method according to claim 1, wherein the cellulose is a cellulose having an O-acyl group bond in the molecule.
である請求項５に記載のカルボン酸エステル系セルロー
ス誘導体の製造方法。6. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 5, wherein the acyl group is a lower aliphatic carbonyl group.
基である請求項６に記載のカルボン酸エステル系セルロ
ース誘導体の製造方法。7. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 6, wherein the lower aliphatic carbonyl group is an acetyl group.
酸、無水テトラヒドロフタル酸、無水ヘキサヒドロフタ
ル酸、無水マレイン酸、無水コハク酸、無水トリメリッ
ト酸の中から選択される請求項１〜７のいずれかに記載
のカルボン酸エステル系セルロース誘導体の製造方法。8. The polyvalent carboxylic acid anhydride is selected from phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, succinic anhydride, and trimellitic anhydride. 7. The method for producing a carboxylic acid ester-based cellulose derivative according to any of 7.
モノカルボン酸との混酸である請求項１〜８のいずれか
に記載のカルボン酸エステル系セルロース誘導体の製造
方法。9. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the polyvalent carboxylic acid anhydride is a mixed acid with an anhydrous monocarboxylic acid anhydride.
酢酸である請求項９に記載のカルボン酸エステル系セル
ロース誘導体の製造方法。10. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 9, wherein the aliphatic monocarboxylic acid anhydride is acetic anhydride.
ス類の１〜１．５倍重量である請求項１〜１０のいずれ
かに記載のカルボン酸エステル系セルロース誘導体の製
造方法。11. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the amount of the acetic acid solvent used is 1 to 1.5 times the weight of the cellulose.
ナトリウムである請求項１〜１１のいずれかに記載のカ
ルボン酸エステル系セルロース誘導体の製造方法。12. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the alkali metal carboxylic acid salt is sodium acetate.
して、０．２〜０．８倍重量である請求項１〜１２のい
ずれかに記載のカルボン酸エステル系セルロース誘導体
の製造方法。13. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the amount of the catalyst used is 0.2 to 0.8 times the weight of the cellulose.
１〜１３のいずれかに記載のカルボン酸エステル系セル
ロース誘導体の製造方法。14. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the twin-screw stirrer is a kneader.
項１〜１４のいずれかに記載のカルボン酸エステル系セ
ルロース誘導体の製造方法。15. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein the reaction temperature is 60 to 110 ° C.
〜１５のいずれかに記載のカルボン酸エステル系セルロ
ース誘導体の製造方法。16. The reaction time is 2 to 8 hours.
16. The method for producing a carboxylic acid ester-based cellulose derivative according to any one of 1 to 15.
えて生成物を析出させる請求項１〜１６のいずれかに記
載のカルボン酸エステル系セルロース誘導体の製造方
法。17. The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, wherein after terminating the reaction, water is added to the reaction solution to precipitate the product.
乾燥させる請求項１〜１７のいずれかに記載のカルボン
酸エステル系セルロース誘導体の製造方法。18. The reaction crude product is purified by washing with water,
The method for producing a carboxylic acid ester-based cellulose derivative according to claim 1, which is dried.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4145846A JP2994857B2 (en) | 1992-06-05 | 1992-06-05 | Method for producing carboxylate-based cellulose derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4145846A JP2994857B2 (en) | 1992-06-05 | 1992-06-05 | Method for producing carboxylate-based cellulose derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05339301A true JPH05339301A (en) | 1993-12-21 |
| JP2994857B2 JP2994857B2 (en) | 1999-12-27 |
Family
ID=15394454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4145846A Expired - Lifetime JP2994857B2 (en) | 1992-06-05 | 1992-06-05 | Method for producing carboxylate-based cellulose derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2994857B2 (en) |
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