JPS59162453A - Analysis of hydroxyalkylcellulose - Google Patents
Analysis of hydroxyalkylcelluloseInfo
- Publication number
- JPS59162453A JPS59162453A JP3700383A JP3700383A JPS59162453A JP S59162453 A JPS59162453 A JP S59162453A JP 3700383 A JP3700383 A JP 3700383A JP 3700383 A JP3700383 A JP 3700383A JP S59162453 A JPS59162453 A JP S59162453A
- Authority
- JP
- Japan
- Prior art keywords
- glycol
- acid
- hydroxyalkylcellulose
- substitution
- ratio
- 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.)
- Pending
Links
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 title claims abstract description 16
- 238000004458 analytical method Methods 0.000 title claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 62
- 238000000034 method Methods 0.000 claims abstract description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 14
- 238000005979 thermal decomposition reaction Methods 0.000 claims abstract description 13
- -1 for example Polymers 0.000 claims abstract description 5
- 238000006467 substitution reaction Methods 0.000 claims abstract 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims 1
- 239000001913 cellulose Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 13
- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 10
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 abstract description 7
- 239000004354 Hydroxyethyl cellulose Substances 0.000 abstract description 7
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000004817 gas chromatography Methods 0.000 abstract description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 239000007787 solid Substances 0.000 abstract description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
- 238000010586 diagram Methods 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- MTVMXNTVZNCVTH-UHFFFAOYSA-N ethane-1,2-diol;2-(2-hydroxyethoxy)ethanol Chemical compound OCCO.OCCOCCO MTVMXNTVZNCVTH-UHFFFAOYSA-N 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000972773 Aulopiformes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000045 pyrolysis gas chromatography Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
Description
【発明の詳細な説明】
本発明はヒドロキシアルキルセルロースの分析方法に係
シ、簡便に、且つ短時間で、しかも固体のまま微量の試
料量で、ヒドロキシアルキルセルロースのＭＳ（モルを
換り、Ｄｓ（を換度）及びＭ Ｂ ／ Ｄ ８比を測定
し得る効果的な分析方法を提供するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for analyzing hydroxyalkyl cellulose, which is simple and quick, and can be carried out by MS (by changing moles, Ds It provides an effective analytical method that can measure the MB/D8 ratio.
従来よシ、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の
ＭＳの定量はモルガン法で行ない、ＤＢはモルガン法で
得られたＭＳの値をもとに１３Ｃ−ＮＭＲで分析を行な
うものであった。Traditionally, MS quantification of hydroxyalkyl cellulose such as hydroxyethyl cellulose and hydroxypropyl cellulose is carried out by the Morgan method, and DB is analyzed by 13C-NMR based on the MS value obtained by the Morgan method. Ta.
しかしながら、従来の上記手法では、モルガン法は操作
が繁雑で時間がかかるという欠点が有り、又、１５０−
ＮＭＲ法は試料を溶媒に溶解させ、更に低粘化させる
必要があるという欠点があった。However, in the conventional above-mentioned method, the Morgan method has the disadvantage that operations are complicated and time-consuming.
The NMR method has the disadvantage that it requires dissolving the sample in a solvent and further reducing the viscosity.
このような状況の下に、本発明者らは種々検討の結果、
被分析試料であるヒドロキシアルキルセルロースに酸を
添加した上で熱分解を行ない、その熱分解生成物をガス
クロマトグラフィー分離して得られるモノアルキレング
リコール、ジアルキレングリコール及びトリアルキレン
グリコールを定量することによシ、ヒドロキシアルキル
セルロースのＭＳ％ Ｄ Ｓ及ヒＭ Ｓ／Ｄ Ｓ比を簡
便に、短時間で、固体のまましかも微量で分析し得るこ
とを見出し、本発明の分析法を確立したのである。Under these circumstances, the inventors of the present invention have conducted various studies and found that
To quantify monoalkylene glycol, dialkylene glycol, and trialkylene glycol obtained by adding acid to hydroxyalkylcellulose, which is the sample to be analyzed, and then performing thermal decomposition, and separating the thermal decomposition products by gas chromatography. The inventors have discovered that the MS% DS and MS/DS ratio of hydroxyalkyl cellulose can be easily analyzed in a short time, in a solid state, and in trace amounts, and have established the analytical method of the present invention. .
即ち、本発明に従えば、先ず被分析試料であるヒドロキ
シアルキルセルロースに酸を添加する。酸としては硫酸
、リン酸、過塩素酸、埴酸及び硝酸等の鉱酸が良い。酸
は直接試料に添加するか、あるいは酸を適当な溶媒（例
えばエーテル、アルコール等）に溶解し、試料に添加し
てもよい。この時、酸の添加量は被分析試料重量に対し
て０．１〜２０重量係が望ましい。That is, according to the present invention, an acid is first added to hydroxyalkylcellulose, which is a sample to be analyzed. As the acid, mineral acids such as sulfuric acid, phosphoric acid, perchloric acid, saline acid and nitric acid are preferred. The acid may be added directly to the sample, or the acid may be dissolved in a suitable solvent (eg, ether, alcohol, etc.) and added to the sample. At this time, the amount of acid added is preferably 0.1 to 20% by weight relative to the weight of the sample to be analyzed.
ついで、酸を添加された試料は熱分解せしめられる。こ
の熱分解に際しては、できるだけ短時間で分解が終了す
ることが望ましく、このためには高周波誘導製熱分解装
置の使用あるいは電気炉への落下方式を取る熱分解装置
を用いることが推奨される。かかる熱分解に際しての温
度は２５０℃〜６００℃の範囲が望ましく、なかでも４
００℃付近の温度において熱分解生成物であるアルキレ
ングリコールの生成が著しいので最も好ましい。The acid-added sample is then pyrolyzed. During this thermal decomposition, it is desirable to complete the decomposition in as short a time as possible, and for this purpose, it is recommended to use a high-frequency induction thermal decomposition device or a thermal decomposition device that uses a dropping method into an electric furnace. The temperature during such thermal decomposition is preferably in the range of 250°C to 600°C, especially 4
It is most preferable at a temperature around 00° C. since alkylene glycol, which is a thermal decomposition product, is produced significantly.
ここで生成した熱分解生成物はガスクロマトグラフィー
にて分離され、モノアルキレングリコール、ジアルキレ
ングリコール及びトリアルキレングリコールの定量がな
され、これらの測定値から被分析試料であるヒドロキシ
アルキルセルロースのＭＳ、ＤＳ及びＭ−８／ Ｄ Ｓ
比を分析し得る。The thermal decomposition products generated here are separated by gas chromatography, and monoalkylene glycol, dialkylene glycol, and trialkylene glycol are quantified. From these measured values, the MS and DS of hydroxyalkyl cellulose, which is the sample to be analyzed, are determined. and M-8/DS
The ratio can be analyzed.
以下、ＭＳ、ＤＢ及びＭＳ／ＤＢ比の分析法を説明する
。Hereinafter, analysis methods for MS, DB, and MS/DB ratio will be explained.
本発明によるＭＳの分析のためにはあらかじめモルガン
法で測定したＭＳと本発明に従って得られたアルキレン
グリコール分析値との関係図が必要となる。−例として
ヒドロキシエチルセルロースの場合、本発明に従って得
られたエチレングリコール及びジエチレングＩＪ ｊ−
ルの測定値に基づくそれらのモル比（エチレングリコー
ル／ジエチレングリコール）を縦軸に、モルガン法で測
定したＭＳを横軸にとり作成した図が第１図である。こ
の第１図が得られれば、ＭＳ未知のヒドロキシエチルセ
ルロースを本発明に従って分析し、その測定値からエチ
レングリコール及びジエチレングリコールのモル比を求
めれば第１図を用いてＭＢ値が得られることになる。因
みに第１図はエチレングリコールドジエチレングリコー
ルのモル比とＭＳとの関係図であるが、必要によりトリ
エチレングリコールの値を考慮に入れても良いわけであ
る。例えばエチレンクリコールドトリエチレンクリコー
ルのモル比、或はジエチレングリコールとトリエチレン
グリコールのモル比とＭＳとの関係図を用いることが出
来る。For MS analysis according to the present invention, a relationship diagram between MS measured by the Morgan method and alkylene glycol analysis values obtained according to the present invention is required in advance. - As an example, in the case of hydroxyethyl cellulose, ethylene glycol and diethylene glycol obtained according to the invention IJ j -
FIG. 1 is a diagram created with the vertical axis representing the molar ratio (ethylene glycol/diethylene glycol) based on the measured values of 100% ethylene glycol and the horizontal axis representing MS measured by the Morgan method. Once this figure 1 is obtained, the MB value can be obtained using figure 1 by analyzing hydroxyethyl cellulose with unknown MS according to the present invention and determining the molar ratio of ethylene glycol and diethylene glycol from the measured values. Incidentally, although FIG. 1 is a diagram showing the relationship between the molar ratio of ethylene glycol diethylene glycol and MS, the value of triethylene glycol may be taken into consideration if necessary. For example, a relationship diagram between MS and the molar ratio of ethylene glycol to triethylene glycol or the molar ratio of diethylene glycol to triethylene glycol can be used.
即ち１本発明に従ってＭＢを求めるためには、あらかじ
めモルガン法で測定したＭＳと本発明に従って得られた
アルキレングリコール分析値との関係図を作成し、これ
を利用してＭＳ未知の試料を分析し得る。因みに、ここ
で作成した関係図は以後常時使用できるわけである。That is, 1. In order to determine MB according to the present invention, a relationship diagram between MS measured by the Morgan method and alkylene glycol analysis values obtained according to the present invention is created in advance, and a sample with unknown MS is analyzed using this. obtain. Incidentally, the relationship diagram created here can be used at any time from now on.
本発明によるＤａの分析は、ヒドロキシアルキルセルロ
ースの被分析試料を本発明方法に従って熱分解−ガスク
ロマトグラフィー分離の処理に付し、得られたモノアル
キレングリコール及びジアルキレングリコールの測定値
と本発明に従って上記の如く得られたＭＢ値とから、次
の式（１）で示した計算式により求めるものである。The analysis of Da according to the present invention involves subjecting a sample of hydroxyalkyl cellulose to be subjected to pyrolysis-gas chromatography separation according to the method of the present invention, and comparing the measured values of monoalkylene glycol and dialkylene glycol obtained according to the present invention. From the MB value obtained as above, it is determined by the calculation formula shown in the following formula (1).
１
ここでＣ□：モノアルキレングリコールの試料１曙当シ
の生成モル数
Ｃ２ニジアルキレングリコールの試料１キ描シの生成モ
ル数
本発明によるＭ Ｓ ／ Ｄ Ｓ比の分析は、ヒドロキ
シアルキルセルロースの被分析試料を本発明に従って分
析し、得られたモノアルキレングリコール及びジアルキ
レングリコールの分析値から、式（２）で示した計算式
によシ求めるものである。1 Where, C□: Number of moles produced in sample 1 of monoalkylene glycol C2 Number of moles produced in sample 1 of didialkylene glycol The analysis of the MS/DS ratio according to the present invention is based on the number of moles produced in sample 1 of monoalkylene glycol. A sample to be analyzed is analyzed according to the present invention, and the obtained analysis values of monoalkylene glycol and dialkylene glycol are used to calculate the value using the calculation formula shown in Equation (2).
ＤＢ Ｏ。DB O.
（ここでＣ工：モノアルキレングリコールの生成モル数
０２ニジアルキレングリコールの生成モル数）
以下、実施例によって本発明を具体的に説明するが、本
発明はこれらの実施例に限定されるものではない。(Here, Step C: Number of moles produced of monoalkylene glycol 02 Number of moles produced of didialkylene glycol) The present invention will be specifically explained below with reference to Examples, but the present invention is not limited to these Examples. do not have.
実施例
ヒドロキシエチルセルロースを本発明に従って分析し、
得られたクロマトグラムを第２図に示した。Example Hydroxyethylcellulose was analyzed according to the invention,
The obtained chromatogram is shown in FIG.
かかるクロマトグラムを求めた実験は、先ず試料１ｆｎ
ｆに硫酸のジエチルエーテル溶液（０，１重量係）３０
μ！を加え、ジエチルエーテルが乾燥したのちに、下記
条件に従って熱分解−ガスクロマトグラフィー分離され
、第２図の如きクロマトグラムが得られたのである。In an experiment to obtain such a chromatogram, first, sample 1fn
F is a diethyl ether solution of sulfuric acid (0.1 weight ratio) 30
μ! After the diethyl ether was dried, it was separated by thermal decomposition and gas chromatography under the following conditions, and the chromatogram shown in FIG. 2 was obtained.
熱分解装置； ＪＨＰ−２型 キューリーポイントパイ
ロライザー〔日本分析工業■
製〕
熱分解温度；６８６℃
キャリアーガス；ヘリウム
流速； ６０ ｒｒｔｌ ／ ｍｉｎ
オーブン温度；１６０℃
パイプ温度；１９０℃
ガスクロマトグラフィー装置；島津ＧＯ−６ＡＭ力 ラ
ム；サーモン！１０００１０チ／クロモソルプＷ−Ａ
Ｖ
温 度；カラム７０℃〜２５０℃ ４℃／ｍｉｎ昇
温 気化室及び検出器２４０
℃
キャリアーガス；ヘリウム
流 速； ６０罰／ｍｉｎ
第２図に示したピーク番号（１）がエチレングリコール
及びピーク番号（２）がジエチレングリコールであり、
これらの成分の面積からエチレングリコール／ジエチレ
ンクリコールのモル比ヲ求めると１．９７となった。こ
の値と第１図よりこコテ分析シたとドロキシエチルセル
ロースのＭ、Ｓは１．８０となシ、別途モルガン法で求
めたＭＳの値（１，７１）と実験誤差内でほぼ一致した
。Thermal decomposition device; JHP-2 type Curie point pyrolyzer [manufactured by Nippon Analytical Industry ■] Thermal decomposition temperature; 686°C Carrier gas; Helium flow rate; 60 rrtl/min Oven temperature; 160°C Pipe temperature; 190°C Gas chromatography device; Shimadzu GO-6AM Power Ram; Salmon! 100010chi/Chromosorp W-A
V Temperature: Column 70°C to 250°C Temperature increase at 4°C/min Vaporization chamber and detector 240°C Carrier gas: Helium flow rate: 60°C/min Peak number (1) shown in Figure 2 is the ethylene glycol peak. Number (2) is diethylene glycol,
The molar ratio of ethylene glycol/diethylene glycol was determined to be 1.97 from the areas of these components. According to this value and FIG. 1, the M and S values of droxyethylcellulose were 1.80, which was approximately equal to the MS value (1,71) separately determined by the Morgan method within experimental error.
父上記式（１）によシ求めたＤＢは、１ｊ９となり、モ
ルガン法で求めたＭＳから１５０−ＮＭＲ法で求めたＤ
Ｂの値（１，１５）と実験誤光内でほぼ一致した。The DB calculated using the above formula (1) is 1j9, and the D calculated using the 150-NMR method from the MS calculated using the Morgan method.
The value of B (1, 15) almost coincided with the experimental error light.
更に、式（２）により求めたＭｅ／ＤＳ比は１．５１と
なり、モルガン法及び’Ｃ！−ＮＭＲ法で求めたＭＥ／
Ｄａ比（１，４９）とこれも実検誤差内でほぼ一致した
。Furthermore, the Me/DS ratio determined by equation (2) is 1.51, and the Morgan method and 'C! -ME determined by NMR method/
This also almost coincided with the Da ratio (1,49) within the actual test error.
このように本発明の方法はヒドロキシアルキルセルロー
スのＭ８％ Ｄ Ｂ 及ヒＭ Ｓ ／ Ｄ Ｓ 比ノ分
析を簡便な方法により短時間で、しかも固体のまま微量
試料量で可能ならしめたものである。As described above, the method of the present invention makes it possible to analyze the M8% DB and MS/DS ratio of hydroxyalkylcellulose in a short time using a simple method, and with a small amount of sample in a solid state. .
４４、図面の簡単な説明
第１図はヒドロキシエチルセルロースヲ本発明に従って
分析し、生成したエチレングリコールドジエチレングリ
コールのモル比を縦軸に、ＭＳを横軸としてグラフにし
たものである。44. Brief Description of the Drawings FIG. 1 is a graph in which hydroxyethyl cellulose was analyzed according to the present invention and the molar ratio of the produced ethylene glycol diethylene glycol is plotted on the vertical axis and MS is plotted on the horizontal axis.
第２図はヒドロキシエチルセルロースの本発明に従って
分析したガスクロマトグラムを表わす。FIG. 2 represents a gas chromatogram of hydroxyethylcellulose analyzed according to the invention.
Claims (1)
、これを熱盆解することにょシ生成したアルキレングリ
コールをガスクロマ８トゲラフイーにて分離せしめ、モ
ノアルキレングリコール、ジアルキレングリコール及ヒ
ドリアルキレングリコールの量を測定し、それらノ値カ
ラヒドロキシアルキルセルロース＋７）モル置換度ＭＳ
、置換度ＤＢ及びＭ Ｓ ／ Ｄ Ｓ比を求める事を特
徴とするヒドロキシアルキルセルロースの分析不法。 ２ 酸が鉱酸である特許請求の範囲第１項記載の方法。 ５ 酸の添加量がヒドロキシアルキルセルロースに対し
て０．１〜２０重量係である特許請求の範囲第１項又は
第２項記載の方法。 ４ 熱分解温度が２５０℃〜６００℃である特許請求の
範囲第１項、第２項又は第３項記載の方法。[Scope of Claims] 1. A small amount of acid is added to hydroxyalkyl cellulose, and the resulting alkylene glycol is separated in a gas chroma 8 togelafie by adding a small amount of acid to the hydroxyalkyl cellulose and disintegrating it in a heat oven. Measure the amount of glycol and calculate their value: Karahydroxyalkyl cellulose + 7) Molar substitution degree MS
Illegal analysis of hydroxyalkyl cellulose characterized by determining the degree of substitution DB and the M S / D S ratio. 2. The method according to claim 1, wherein the acid is a mineral acid. 5. The method according to claim 1 or 2, wherein the amount of the acid added is 0.1 to 20% by weight based on the hydroxyalkylcellulose. 4. The method according to claim 1, 2 or 3, wherein the thermal decomposition temperature is 250°C to 600°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3700383A JPS59162453A (en) | 1983-03-07 | 1983-03-07 | Analysis of hydroxyalkylcellulose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3700383A JPS59162453A (en) | 1983-03-07 | 1983-03-07 | Analysis of hydroxyalkylcellulose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59162453A true JPS59162453A (en) | 1984-09-13 |
Family
ID=12485525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3700383A Pending JPS59162453A (en) | 1983-03-07 | 1983-03-07 | Analysis of hydroxyalkylcellulose |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59162453A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105136710A (en) * | 2015-09-11 | 2015-12-09 | 青岛科技大学 | Determination method of hydroxypropyl chitosan substitution degree |
| CN105203493A (en) * | 2015-09-11 | 2015-12-30 | 青岛科技大学 | Method for determining substitution degree of hydroxypropyl chitosan |
| CN105277507A (en) * | 2015-09-11 | 2016-01-27 | 青岛科技大学 | Hydroxypropyl chitosan substitution degree determination method |
| CN105300916A (en) * | 2015-09-11 | 2016-02-03 | 青岛科技大学 | Determination method of hydroxypropyl chitosan substitution degree |
-
1983
- 1983-03-07 JP JP3700383A patent/JPS59162453A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105136710A (en) * | 2015-09-11 | 2015-12-09 | 青岛科技大学 | Determination method of hydroxypropyl chitosan substitution degree |
| CN105203493A (en) * | 2015-09-11 | 2015-12-30 | 青岛科技大学 | Method for determining substitution degree of hydroxypropyl chitosan |
| CN105277507A (en) * | 2015-09-11 | 2016-01-27 | 青岛科技大学 | Hydroxypropyl chitosan substitution degree determination method |
| CN105300916A (en) * | 2015-09-11 | 2016-02-03 | 青岛科技大学 | Determination method of hydroxypropyl chitosan substitution degree |
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