JP2001031701A - Low substituted hydroxypropyl cellulose - Google Patents
Low substituted hydroxypropyl celluloseInfo
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- JP2001031701A JP2001031701A JP2000144253A JP2000144253A JP2001031701A JP 2001031701 A JP2001031701 A JP 2001031701A JP 2000144253 A JP2000144253 A JP 2000144253A JP 2000144253 A JP2000144253 A JP 2000144253A JP 2001031701 A JP2001031701 A JP 2001031701A
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- Prior art keywords
- low
- substituted hydroxypropylcellulose
- polymerization
- average degree
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Abstract
(57)【要約】
【課題】 良好な粒状特性、錠剤性能を有する低置換度
ヒドロキシプロピルセルロースを提供する。
【解決手段】 ヒドロキシプロポキシル基の含有量が
５．０〜１６．０重量％であり、かつ、見かけの平均重
合度が３５０〜７００である低置換度ヒドロキシプロピ
ルセルロースによる。PROBLEM TO BE SOLVED: To provide a low-substituted hydroxypropylcellulose having good granular properties and tablet performance. A low-substituted hydroxypropylcellulose having a hydroxypropoxyl group content of 5.0 to 16.0% by weight and an apparent average degree of polymerization of 350 to 700.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、良好な粒状特性、
錠剤性能を有する低置換度ヒドロキシプロピルセルロー
スに関する。FIELD OF THE INVENTION The present invention relates to
It relates to a low-substituted hydroxypropylcellulose having tablet performance.
【０００２】[0002]
【従来の技術】ヒドロキシプロピルセルロースは、セル
ロースの構成単位であるグルコース（Ｃ6Ｈ10Ｏ5）単位
の水酸基をヒドロキシプロピル基でエーテル化した非イ
オン性ポリマーで、様々な特性を有することから広い用
途分野に利用されている。一般にヒドロキシプロピルセ
ルロースとは、ヒドロキシプロポキシル基の含有量が５
０〜８０重量％のものをいい、含有量が５．０〜１６．
０重量％のものは、低置換度ヒドロキシプロピルセルロ
ースといい、その性質は通常のヒドロキシプロピルセル
ロースと異にする。2. Description of the Related Art Hydroxypropylcellulose is a nonionic polymer obtained by etherifying a hydroxyl group of glucose (C 6 H 10 O 5 ) unit, which is a constituent unit of cellulose, with a hydroxypropyl group. Used in application fields. Generally, hydroxypropylcellulose has a hydroxypropoxyl group content of 5%.
0 to 80% by weight, having a content of 5.0 to 16.
Those having 0% by weight are called low-substituted hydroxypropylcellulose, and their properties are different from ordinary hydroxypropylcellulose.
【０００３】両者の相違点は、水への溶解性にあり、ヒ
ドロキシプロピルセルロースが水溶性であるのに対し、
低置換度ヒドロキシプロピルセルロースが水には不溶性
であるが、吸水して膨潤する点にある。この性質を利用
して、低置換度ヒドロキシプロピルセルロースは主とし
て経口固形医薬製剤の崩壊剤として使用される。また、
低置換度ヒドロキシプロピルセルロースは繊維状である
ため、錠剤の硬度を高める作用を有することから乾式結
合剤として用いることができ、さらに水との練合物が結
合性を持つことから湿式結合剤としても用いることがで
きる。[0003] The difference between the two is in the solubility in water, whereas hydroxypropyl cellulose is water-soluble,
Low-substituted hydroxypropylcellulose is insoluble in water, but swells by absorbing water. Utilizing this property, low-substituted hydroxypropylcellulose is mainly used as a disintegrant for oral solid pharmaceutical preparations. Also,
Since low-substituted hydroxypropylcellulose is fibrous, it can be used as a dry binder because it has the effect of increasing the hardness of the tablet, and as a wet binder because the kneaded product with water has binding properties. Can also be used.
【０００４】[0004]
【発明が解決しようとする課題】一般に湿式造粒は、流
動性の悪い原料粉末の流動性を高める目的で行われる
が、造粒物の品質、すなわち粒度分布や造粒物の強度、
造粒物を打錠して得られる錠剤の硬度や崩壊性は、主と
して結合剤の性質に左右される。そして、低置換度ヒド
ロキシプロピルセルロースの場合、置換度、粒度が結合
性に影響を与える重要な因子と考えられてきたが、これ
らの因子を制御しても、造粒が異常に亢進して錠剤の崩
壊が遅延したり、造粒性が不足して錠剤の硬度が低下す
ることがしばしば認められてきた。Generally, wet granulation is performed for the purpose of increasing the flowability of raw material powder having poor flowability. However, the quality of the granulated material, that is, the particle size distribution, the strength of the granulated material,
The hardness and disintegration of a tablet obtained by tableting the granulated product mainly depend on the properties of the binder. In the case of low-substituted hydroxypropylcellulose, the degree of substitution and particle size have been considered to be important factors affecting the binding properties, but even if these factors are controlled, granulation is abnormally enhanced and tablets It has been often observed that the disintegration of the tablets is delayed or the tableting hardness is reduced due to insufficient granulation.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、このよう
な従来の欠点を改良すべく、鋭意検討した結果、低置換
度ヒドロキシプロピルセルロースの重合度又は分子量が
湿式造粒における結合性に影響することを見出し、本発
明を完成させた。すなわち、本発明は、ヒドロキシプロ
ポキシル基の含有量が５．０〜１６．０重量％であり、
かつ、見かけの平均重合度が３５０〜７００であること
特徴とする低置換度ヒドロキシプロピルセルロースを提
供するものである。Means for Solving the Problems The inventors of the present invention have conducted intensive studies in order to improve such conventional drawbacks. As a result, the degree of polymerization or the molecular weight of the low-substituted hydroxypropylcellulose has been found to decrease the binding property in wet granulation. The inventor has found that it has an effect, and completed the present invention. That is, in the present invention, the content of the hydroxypropoxyl group is 5.0 to 16.0% by weight,
Further, the present invention provides a low-substituted hydroxypropylcellulose having an apparent average degree of polymerization of 350 to 700.
【０００６】[0006]
【発明の実施の形態】以下に、本発明を詳細に説明す
る。本発明の低置換度ヒドロキシプロピルセルロース
は、ヒドロキシプロポキシル基の含有量が５．０〜１
６．０重量％である。なお、ヒドロキシプロポキシル基
の含有量は、日本薬局方の「低置換度ヒドロキシプロピ
ルセルロース」の項に収載された定量法によって得るこ
とができる。DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail. The low-substituted hydroxypropylcellulose of the present invention has a hydroxypropoxyl group content of 5.0 to 1%.
6.0% by weight. In addition, the content of the hydroxypropoxyl group can be obtained by the quantitative method described in the section of “Low-substituted hydroxypropylcellulose” in the Japanese Pharmacopoeia.
【０００７】次に、本発明の低置換度ヒドロキシプロピ
ルセルロースの見かけの平均重合度について説明する。
一般に結合剤の重合度（分子量）が結合力に影響するこ
とは公知であるが、これは、通常の結合剤は水等の溶媒
に溶解して結合作用を発現して、この時の溶液の粘性が
重合度に依存するためと考えられている。しかし、低置
換度ヒドロキシプロピルセルロースは、湿式造粒におい
ても溶媒には溶解しないため、重合度は直接造粒性とは
無関係であると考えられてきた。このため、低置換度ヒ
ドロキシプロピルセルロースにおいて、その重合度（分
子量）との関係についてはこれまで全く示されていなか
った。ところが、驚くべきことに溶媒に溶けなくても特
定の重合度の低置換度ヒドロキシプロピルセルロースが
安定した造粒特性を与えることを本発明者が見出した。
これは、通常の結合剤とは異なった機構により結合性を
発揮するためと思われる。Next, the apparent average degree of polymerization of the low-substituted hydroxypropylcellulose of the present invention will be described.
It is generally known that the degree of polymerization (molecular weight) of a binder affects the bonding strength. This is because a normal binder dissolves in a solvent such as water to exhibit a binding action, and the It is believed that the viscosity depends on the degree of polymerization. However, since low-substituted hydroxypropylcellulose does not dissolve in a solvent even in wet granulation, it has been considered that the degree of polymerization is not directly related to granulation properties. Therefore, the relationship between the degree of polymerization (molecular weight) and the degree of polymerization of low-substituted hydroxypropylcellulose has not been shown at all. However, the present inventors have surprisingly found that a low-substituted hydroxypropylcellulose having a specific degree of polymerization provides stable granulation properties even if it is not soluble in a solvent.
This seems to be due to the fact that the binding agent exerts binding properties by a different mechanism from ordinary binding agents.
【０００８】本発明において低置換度ヒドロキシプロピ
ルセルロースの見かけの平均重合度とは、公定書（ＡＳ
ＴＭ Ｄ１７９５−６２）に記載されている低置換度ヒ
ドロキシプロピルセルロースの原料であるセルロース
（パルプ）の平均重合度の測定法と同様な方法により測
定した時の平均重合度として算出される値をいうことと
した。この方法は、試料を銅エチレンジアミン試液に溶
解した液の動粘度と溶媒の動粘度から相対粘度を求め、
それから固有粘度を算出し、さらに係数を掛けて平均重
合度とするものである。この場合の係数は、セルロース
についての係数なので、低置換度ヒドロキシプロピルセ
ルロースについては別途係数を求めなければならない。
しかし、低置換度ヒドロキシプロピルセルロースはセル
ロースにわずかな量の置換基を導入しただけであるの
で、セルロースの場合と比較して大差はないものと仮定
して、セルロースの係数をそのまま準用して、見かけの
平均重合度とした。In the present invention, the apparent average degree of polymerization of the low-substituted hydroxypropylcellulose is defined as the official standard (AS
TM D1795-62), a value calculated as an average degree of polymerization when measured by a method similar to the method for measuring the average degree of polymerization of cellulose (pulp) as a raw material of low-substituted hydroxypropylcellulose described in TM D1795-62). I decided that. In this method, the relative viscosity is determined from the kinematic viscosity of the solution obtained by dissolving the sample in the copper ethylenediamine TS and the kinematic viscosity of the solvent,
Then, the intrinsic viscosity is calculated and further multiplied by a coefficient to obtain an average degree of polymerization. Since the coefficient in this case is a coefficient for cellulose, a coefficient must be separately obtained for low-substituted hydroxypropylcellulose.
However, low-substituted hydroxypropylcellulose only introduces a small amount of substituents to cellulose, so assuming that there is not much difference compared to the case of cellulose, applying the coefficient of cellulose as it is, The average degree of polymerization was apparent.
【０００９】本発明の低置換度ヒドロキシプロピルセル
ロースは、見かけの平均重合度が３５０〜７００、好ま
しくは４００〜６００である。見かけの平均重合度は、
低置換度ヒドロキシプロピルセルロースの製造工程にお
いて原料重合度、反応温度、反応時間、その他の工程パ
ラメーターを適宜コントロールすることにより制御され
るが、３５０より低い場合は、撹拌造粒が異常に亢進
し、造粒物の強度が高くなり打錠物の崩壊時間が長くな
る。一方、見かけの平均重合度が７００を超える場合
は、造粒が進まず、顆粒強度が不足して打錠物の硬度が
不足する。The low-substituted hydroxypropylcellulose of the present invention has an apparent average degree of polymerization of 350 to 700, preferably 400 to 600. The apparent average degree of polymerization is
In the production process of low-substituted hydroxypropylcellulose, the degree of polymerization of the raw material, the reaction temperature, the reaction time, and other process parameters are controlled by appropriately controlling, but when it is lower than 350, stirring granulation is abnormally enhanced, The strength of the granulated material is increased, and the disintegration time of the tablet is prolonged. On the other hand, when the apparent average degree of polymerization exceeds 700, granulation does not proceed, the granule strength is insufficient, and the hardness of the tablet is insufficient.
【００１０】本発明の低置換度ヒドロキシプロピルセル
ロースは、上記物性のほかに乾式レーザー回折法による
体積平均粒径が１０〜１００μｍであることが好まし
い。平均粒径がこの範囲より小さい場合は、激しく粉砕
されているため見かけの平均重合度を３５０〜７００に
維持することが困難となり、湿式造粒において結合性が
異常に亢進するおそれがある。一方、平均粒径がこの範
囲より大きい場合は湿式造粒に適さないおそれがある。
なお、乾式レーザー回折法とは、圧縮空気で粉体サンプ
ルを噴出させたものにレーザー光を照射し、その回折強
度により体積平均径を測定する方法をいう。例えば、Ro
dos & Helos 社のレーザー回折式粒度測定機が挙げられ
る。体積平均粒径は、例えば「改訂増補粉体物性図説」
粉体工学会・日本粉体工業技術協会編、日経技術図書、
１９８５年、第８８頁に記載されているように、式｛Σ
(ｎＤ3)／Σｎ｝1/3を用いて計算される。式中、Ｄは粒
子の直径、ｎはその直径の粒子数、Σｎは全粒子数を表
す。The low-substituted hydroxypropylcellulose of the present invention preferably has a volume average particle size of 10 to 100 μm as measured by a dry laser diffraction method in addition to the above physical properties. If the average particle size is smaller than this range, it is difficult to maintain an apparent average polymerization degree of 350 to 700 due to vigorous pulverization, and there is a possibility that the binding property may be abnormally enhanced in wet granulation. On the other hand, when the average particle size is larger than this range, there is a possibility that it is not suitable for wet granulation.
Note that the dry laser diffraction method refers to a method of irradiating a laser beam onto a powder sample ejected with compressed air and measuring the volume average diameter based on the diffraction intensity. For example, Ro
Dos & Helos laser diffraction particle size analyzer. The volume average particle size is, for example, "Revised supplementary powder physical properties illustration"
Japan Society of Powder Technology, Japan Society of Powder Technology, Nikkei Technical Books,
As described on page 88 of 1985, the formula
Calculated using (nD 3 ) / {n} 1/3 . In the formula, D is the diameter of the particle, n is the number of particles of that diameter, and Δn is the total number of particles.
【００１１】また、かさ密度（固め）は０.４〜０.８
ｇ／ｍｌが好ましい。かさ密度（固め）が ０.４ｇ／ｍ
ｌ未満では流動性に乏しく、実用的でない。一方、０.
８ｇ／ｍｌを越えるものは圧縮成型時の硬度発現が低く
なる。なお、このかさ密度の測定は、直径５.０３ｃ
ｍ、高さ５.０３ｃｍ（容積１００ｍｌ）の円筒容器へ
試料をＪＩＳ２２メッシュ（７１０μｍ）の篩を通して
２３ｃｍ上方から均一に供給し、上面をすり切った後、
容器にホソカワミクロン社製パウダーテスターの備品で
ある専用キャップをはめ、この上縁まで粉体を加えてタ
ップ高さ１.８ｃｍのタッピングを１８０回行う。終了
後、キャップをはずして容器の上面で粉体をすり切って
秤量し、この状態の測定値をかさ密度とする。これらの
操作は、ホソカワミクロン社製パウダーテスター（ＰＴ
−Ｄ）を使用することにより測定できる。Further, the bulk density (consolidation) is 0.4 to 0.8.
g / ml is preferred. Bulk density (consolidated) 0.4 g / m
If it is less than 1, the fluidity is poor and it is not practical. On the other hand, 0.
If the amount exceeds 8 g / ml, the hardness at the time of compression molding becomes low. The bulk density was measured using a diameter of 5.03c.
m, a sample was fed uniformly through a JIS22 mesh (710 μm) sieve into a cylindrical container having a height of 5.03 cm (volume: 100 ml) from a height of 23 cm, and the top surface was cut off.
The container is fitted with a special cap as a fixture of a powder tester manufactured by Hosokawa Micron Corporation, and powder is added to the upper edge of the container, and tapping is performed 180 times with a tap height of 1.8 cm. After completion, the cap is removed, the powder is ground on the upper surface of the container and weighed, and the measured value in this state is defined as the bulk density. These operations were performed using a powder tester manufactured by Hosokawa Micron (PT
-D) can be measured.
【００１２】本発明の低置換度ヒドロキシプロピルセル
ロースの造粒方法は、特に限定されず、公知の方法が用
いられる。錠剤の製造方法についても、特に限定され
ず、公知の方法が用いられる。錠剤には、本発明の低置
換度ヒドロキシプロピルセルロースのほか、例えば、主
薬、ステアリン酸マグネシウム等の滑沢剤、コーンスタ
ーチや乳糖などの賦形剤、他の崩壊剤や結合剤などを含
むことができる。本発明の低置換度ヒドロキシプロピル
セルロースの錠剤中の含有量は、特に限定されないが、
好ましくは５〜５０重量％の範囲である。The method for granulating the low-substituted hydroxypropylcellulose of the present invention is not particularly limited, and a known method is used. The method for producing the tablet is not particularly limited, either, and a known method is used. In the tablet, in addition to the low-substituted hydroxypropylcellulose of the present invention, for example, the base drug, a lubricant such as magnesium stearate, an excipient such as corn starch or lactose, and other disintegrants and binders may be included. it can. The content of the low-substituted hydroxypropylcellulose in the tablet of the present invention is not particularly limited,
Preferably it is in the range of 5 to 50% by weight.
【００１３】[0013]
【実施例】以下、本発明を実施例及び比較例によってさ
らに詳細に説明するが、本発明はこれらの実施例の記載
に限定されるものではない。 実施例１ 木材パルプを４９重量％水酸化ナトリウム水溶液に浸漬
後、圧搾してアルカリセルロースを得た。このアルカリ
セルロース８００ｇを反応機に仕込み、窒素置換を行っ
た後に、酸化プロピレン８５.６ｇを加えて撹拌しなが
ら４０℃で１時間、さらに７０℃で１時間反応して反応
物を得た。５リットルの双腕ニーダーに６５℃の熱水２
リットルを入れ、反応物を投入して約１０分練合した
後、酢酸で中和して晶出させた。これを９０℃の熱水で
洗浄後、圧搾して脱水し、乾燥した後に、高速回転衝撃
粉砕機で粉砕してヒドロキシプロポキシル基の含有量が
１１.０重量％、見かけの平均重合度が５３０の低置換
度ヒドロキシプロピルセルロースを得た。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples. Example 1 Wood pulp was immersed in a 49% by weight aqueous solution of sodium hydroxide and pressed to obtain alkali cellulose. After 800 g of the alkali cellulose was charged into the reactor and purged with nitrogen, 85.6 g of propylene oxide was added, and the mixture was reacted at 40 ° C. for 1 hour with stirring and further at 70 ° C. for 1 hour to obtain a reaction product. 65 ℃ hot water 2 in a 5 liter double arm kneader
One liter was added, and the reaction product was charged and kneaded for about 10 minutes, and then neutralized with acetic acid for crystallization. This was washed with hot water at 90 ° C., squeezed and dehydrated, dried, and then crushed by a high-speed rotary impact crusher to have a hydroxypropoxyl group content of 11.0% by weight and an apparent average degree of polymerization. 530 low-substituted hydroxypropylcellulose was obtained.
【００１４】実施例２〜５、比較例１〜３ ヒドロキシプロポキシル基の含有量及び見かけの平均重
合度以外は、実施例１と同様な方法で、低置換度ヒドロ
キシプロピルセルロースを調製した。その結果を表１に
示す。Examples 2-5, Comparative Examples 1-3 Low-substituted hydroxypropylcellulose was prepared in the same manner as in Example 1, except for the content of hydroxypropoxyl group and the apparent average degree of polymerization. Table 1 shows the results.
【００１５】上記実施例及び比較例により得られた低置
換度ヒドロキシプロピルセルロースについて、以下の各
条件で測定を行った。 １）撹拌造粒 乳糖７０重量％、低置換度ヒドロキシプロピルセルロー
ス３０重量％の割合で混合し、その２００ｇを撹拌造粒
装置（パウレック社製バーチカルグラニュレーターＶＧ
−２５）に入れて、ヒドロキシプロピルセルロース（日
本曹達製ＨＰＣ−Ｌ、１重量％水溶液１４０ｇ）を結合
剤として撹拌造粒を行った。造粒物を６０℃で一晩静置
乾燥して得た。造粒物の粒度分布を篩により測定し、平
均粒子径を求めた。The low-substituted hydroxypropylcellulose obtained in the above Examples and Comparative Examples was measured under the following conditions. 1) Stirring granulation 70% by weight of lactose and 30% by weight of low-substituted hydroxypropylcellulose were mixed, and 200 g of the mixture was stirred with a stirring granulator (Vertical Granulator VG manufactured by Powrex).
-25), and subjected to stirring granulation using hydroxypropyl cellulose (HPC-L manufactured by Nippon Soda, 140 g of a 1% by weight aqueous solution) as a binder. The granules were obtained by drying at 60 ° C. overnight. The particle size distribution of the granulated product was measured with a sieve, and the average particle size was determined.
【００１６】２）打錠試験 造粒物に ０.５重量％の割合でステアリン酸マグネシウ
ムを混合し、ロータリー打錠機で打錠（直径８ｍｍ、打
錠圧力１ｔ）して錠剤とした。錠剤の硬度をエルウェカ
硬度計で測定し、崩壊試験を日本薬局方の方法により測
定した。結果を表１に示す。2) Tableting test Magnesium stearate was mixed with the granulated product at a ratio of 0.5% by weight, and the mixture was tableted (diameter: 8 mm, tableting pressure: 1 t) with a rotary tableting machine to obtain tablets. The tablet hardness was measured with an Elweka hardness tester, and the disintegration test was measured by the method of the Japanese Pharmacopoeia. Table 1 shows the results.
【００１７】[0017]
【表１】 （注１)「ヒドロキシプロポキシル基の含有量」は、日
本薬局方に従い測定した。 （注２）「見かけの平均重合度」は、ASTM D1795-62に
従い測定した。 （注３）「平均粒子径」は、Rodos&Helos社製レーザー
回折式粒度測定機を用いて測定した。[Table 1] (Note 1) “Content of hydroxypropoxyl group” was measured according to the Japanese Pharmacopoeia. (Note 2) “Apparent average degree of polymerization” was measured according to ASTM D1795-62. (Note 3) “Average particle size” was measured using a laser diffraction type particle size analyzer manufactured by Rodos & Helos.
【００１８】表１に示す通り、見かけの平均重合度を３
５０〜７００に調節した低置換度ヒドロキシプロピルセ
ルロースは、良好な造粒特性及び錠剤性能を与える。As shown in Table 1, the apparent average degree of polymerization was 3
Low substituted hydroxypropylcellulose adjusted to 50-700 gives good granulation properties and tablet performance.
【００１９】[0019]
【発明の効果】本発明の低置換度ヒドロキシプロピルセ
ルロースを用いることにより、良好な造粒特性及び錠剤
性能を得ることが可能となる。By using the low-substituted hydroxypropylcellulose of the present invention, good granulation characteristics and tablet performance can be obtained.
Claims (4)
５．０〜１６．０重量％であり、かつ、見かけの平均重
合度が３５０〜７００であることを特徴とする低置換度
ヒドロキシプロピルセルロース。1. A low-substituted hydroxypropylcellulose having a hydroxypropoxyl group content of 5.0 to 16.0% by weight and an apparent average degree of polymerization of 350 to 700.
００であることを特徴とする請求項１に記載の低置換度
ヒドロキシプロピルセルロース。2. The apparent average degree of polymerization is 400 to 6
2. The low-substituted hydroxypropylcellulose according to claim 1, wherein
平均粒径が、１０〜１００μｍであることを特徴とする
請求項１又は請求項２に記載の低置換度ヒドロキシプロ
ピルセルロース。3. The low-substituted hydroxypropyl cellulose according to claim 1, wherein the volume average particle diameter determined by dry laser diffraction is 10 to 100 μm.
８ｇ／ｍｌであることを特徴とする請求項１〜３のいず
れかに記載の低置換度ヒドロキシプロピルセルロース。4. The method according to claim 1, wherein the bulk density is 0.4 to 0.5.
The low-substituted hydroxypropylcellulose according to any one of claims 1 to 3, which is 8 g / ml.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000144253A JP2001031701A (en) | 1999-05-18 | 2000-05-17 | Low substituted hydroxypropyl cellulose |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13678799 | 1999-05-18 | ||
| JP11-136787 | 1999-05-18 | ||
| JP2000144253A JP2001031701A (en) | 1999-05-18 | 2000-05-17 | Low substituted hydroxypropyl cellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001031701A true JP2001031701A (en) | 2001-02-06 |
Family
ID=26470290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000144253A Pending JP2001031701A (en) | 1999-05-18 | 2000-05-17 | Low substituted hydroxypropyl cellulose |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2001031701A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351853B2 (en) | 2006-01-23 | 2008-04-01 | Albion Advanced Nutrition | Method of manufacturing a granular mineral composition |
| JP2010254756A (en) * | 2009-04-22 | 2010-11-11 | Shin-Etsu Chemical Co Ltd | High moldability, high fluidity, low substituted hydroxypropyl cellulose and solid preparation containing the same |
| WO2011027728A1 (en) | 2009-09-02 | 2011-03-10 | 日本曹達株式会社 | Coating agent comprising hydroxyalkyl cellulose |
| JP2011195665A (en) * | 2010-03-18 | 2011-10-06 | Shin-Etsu Chemical Co Ltd | Low-substituted hydroxypropyl cellulose and solid formulation including the same |
| WO2014203819A1 (en) | 2013-06-17 | 2014-12-24 | 日本曹達株式会社 | Coating agent containing hydroxyalkyl cellulose |
| JP2015096490A (en) * | 2013-10-08 | 2015-05-21 | 大正製薬株式会社 | Solid preparations |
| EP3284485A1 (en) | 2016-08-16 | 2018-02-21 | Shin-Etsu Chemical Co., Ltd. | Low-substituted hydroxypropyl cellulose and solid preparation |
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| JPS55137102A (en) * | 1979-04-12 | 1980-10-25 | Yamanouchi Pharmaceut Co Ltd | Aqueous gelatinous low-substituted hydroxypropyl cellulose, dried solid thereof and production thereof |
| JPH10259201A (en) * | 1997-03-21 | 1998-09-29 | Shin Etsu Chem Co Ltd | Low-substituted hydroxypropylcellulose, composition and production method thereof |
| JPH10279601A (en) * | 1997-04-08 | 1998-10-20 | Shin Etsu Chem Co Ltd | Low substituted hydroxypropylcellulose powder |
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| JPS5163927A (en) * | 1974-11-28 | 1976-06-02 | Shinetsu Chemical Co | Ketsugoseiryokonajozaihokaizaino seizohoho |
| JPS55137102A (en) * | 1979-04-12 | 1980-10-25 | Yamanouchi Pharmaceut Co Ltd | Aqueous gelatinous low-substituted hydroxypropyl cellulose, dried solid thereof and production thereof |
| JPH10259201A (en) * | 1997-03-21 | 1998-09-29 | Shin Etsu Chem Co Ltd | Low-substituted hydroxypropylcellulose, composition and production method thereof |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7351853B2 (en) | 2006-01-23 | 2008-04-01 | Albion Advanced Nutrition | Method of manufacturing a granular mineral composition |
| JP2010254756A (en) * | 2009-04-22 | 2010-11-11 | Shin-Etsu Chemical Co Ltd | High moldability, high fluidity, low substituted hydroxypropyl cellulose and solid preparation containing the same |
| US9040686B2 (en) | 2009-09-02 | 2015-05-26 | Nippon Soda Co., Ltd. | Coating agent comprising hydroxyalkyl cellulose |
| WO2011027728A1 (en) | 2009-09-02 | 2011-03-10 | 日本曹達株式会社 | Coating agent comprising hydroxyalkyl cellulose |
| JP2011195665A (en) * | 2010-03-18 | 2011-10-06 | Shin-Etsu Chemical Co Ltd | Low-substituted hydroxypropyl cellulose and solid formulation including the same |
| WO2014203819A1 (en) | 2013-06-17 | 2014-12-24 | 日本曹達株式会社 | Coating agent containing hydroxyalkyl cellulose |
| KR20150144800A (en) | 2013-06-17 | 2015-12-28 | 닛뽕소다 가부시키가이샤 | Coating agent containing hydroxyalkyl cellulose |
| JP2015096490A (en) * | 2013-10-08 | 2015-05-21 | 大正製薬株式会社 | Solid preparations |
| EP3284485A1 (en) | 2016-08-16 | 2018-02-21 | Shin-Etsu Chemical Co., Ltd. | Low-substituted hydroxypropyl cellulose and solid preparation |
| JP2018028002A (en) * | 2016-08-16 | 2018-02-22 | 信越化学工業株式会社 | Low substituted hydroxypropyl cellulose and solid preparation |
| KR20180019486A (en) * | 2016-08-16 | 2018-02-26 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Low-substituted hydroxypropyl cellulose and solid preparation |
| US10959959B2 (en) | 2016-08-16 | 2021-03-30 | Shin-Etsu Chemical Co., Ltd. | Low-substituted hydroxypropyl cellulose and solid preparation |
| KR102333973B1 (en) | 2016-08-16 | 2021-12-03 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Low-substituted hydroxypropyl cellulose and solid preparation |
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