JPH03229701A - Production of cation-modified starch - Google Patents
Production of cation-modified starchInfo
- Publication number
- JPH03229701A JPH03229701A JP2026562A JP2656290A JPH03229701A JP H03229701 A JPH03229701 A JP H03229701A JP 2026562 A JP2026562 A JP 2026562A JP 2656290 A JP2656290 A JP 2656290A JP H03229701 A JPH03229701 A JP H03229701A
- Authority
- JP
- Japan
- Prior art keywords
- starch
- modified starch
- cation
- reaction
- water
- 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
- 229920000881 Modified starch Polymers 0.000 title claims abstract description 20
- 239000004368 Modified starch Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 25
- 229920002472 Starch Polymers 0.000 claims abstract description 22
- 235000019698 starch Nutrition 0.000 claims abstract description 22
- 239000008107 starch Substances 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 239000002002 slurry Substances 0.000 claims abstract description 4
- 235000019426 modified starch Nutrition 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 27
- 239000003795 chemical substances by application Substances 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 12
- 238000000034 method Methods 0.000 abstract description 7
- 238000007796 conventional method Methods 0.000 abstract description 2
- 150000004820 halides Chemical class 0.000 abstract description 2
- 150000003944 halohydrins Chemical group 0.000 abstract description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- -1 trialkylammonium halide Chemical class 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は澱粉をカチオン化剤で処理して、カチオン変性
澱粉を製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing cationically modified starch by treating starch with a cationizing agent.
更に詳しくは、製紙用薬剤、繊維処理剤、凝集剤、乳化
剤などの用途に多量に使用されているカチオン変性澱粉
について、従来の製造方法に比べ、より短時間で反応が
進行し、より高反応率となりその結果、生産性、歩留り
、経済性に優れたカチオン変性澱粉の製造方法に関する
ものである。More specifically, regarding cation-modified starch, which is used in large quantities for applications such as paper-making agents, fiber treatment agents, flocculants, and emulsifiers, the reaction proceeds in a shorter time than with conventional production methods, resulting in a higher reaction rate. The present invention relates to a method for producing cationically modified starch that has excellent productivity, yield, and economical efficiency.
［従来の技術］
一般にカチオン変性天然高分子化合物は、凝集剤、製紙
業における紙力増強剤、填料保持剤、繊維などに対する
帯電防止剤、柔軟仕上剤あるいは、化粧品、シャンプー
などの配合剤として、近年広く利用されてきている。こ
の中で化粧品、シャンプー、リンスなどの配合剤として
使用する場合は、その効果が顕著であることと共に、人
体に対する安全性が高く、使用感が良好であり、このも
のを合成するには、グリシジルトリアルキルアンモニウ
ムハライドをカチオン化剤として使用したカチオン変性
セルロースが製造されている。また、カチオン変性澱粉
については、紙用の紙力増強剤、中性抄紙剤用の、填料
歩留り向上剤としての効果もあり、現在徐々に使用され
ている。[Prior Art] Cation-modified natural polymer compounds are generally used as flocculants, paper strength enhancers in the paper industry, filler retention agents, antistatic agents for fibers, fabric softeners, or compounding agents in cosmetics, shampoos, etc. It has been widely used in recent years. Among these, when used as a compounding agent in cosmetics, shampoos, conditioners, etc., it has a remarkable effect, is highly safe for the human body, and has a good feeling of use. Cationically modified cellulose has been produced using trialkylammonium halide as a cationizing agent. Furthermore, cationically modified starch is effective as a paper strength enhancer for paper and a filler retention improver for neutral papermaking agents, and is now gradually being used.
「発明が解決しようとする問題点」
カチオン変性澱粉の製造方法としては、従来澱粉を水に
分散させ、触媒として、水酸化ナトリウムを用いて、ハ
ロヒドリン基を持つ第四級アンモニウム塩と反応させる
方法で製造されている。しかしながら、この方法では、
反応時間が長くかかり、反応率６０％以上のものを得る
ためには、４〜８時間もの反応時間が必要であった。従
って１〜２時間以内という短時間で反応率５０％以上と
することは困難であり、このため、抄紙の前段階でカチ
オン変性澱粉を合成し、そのまま使用する際には、■工
程当たりの時間が長くかかり過ぎ、よって時間的、経済
的なロスが多くなるため、より短時間で、反応を終了す
ることが以前より求められていた。"Problems to be Solved by the Invention" Conventional methods for producing cationically modified starch include dispersing starch in water and reacting it with a quaternary ammonium salt having a halohydrin group using sodium hydroxide as a catalyst. Manufactured in However, with this method,
The reaction time was long, and in order to obtain a reaction rate of 60% or more, a reaction time of 4 to 8 hours was required. Therefore, it is difficult to achieve a reaction rate of 50% or more in a short period of time, such as within 1 to 2 hours.For this reason, when cationically modified starch is synthesized before papermaking and used as it is, Since this process takes too long, resulting in a lot of time and economic loss, it has been desired to complete the reaction in a shorter period of time.
［問題点を解決するための手段］
本発明者らは、上記方法の欠点を克服したカチオン変性
澱分の製造方法を開発するため、鋭意研究を重ねた結果
、澱粉を水に分散させ、触媒として水酸化カリウムを用
い、またカチオン化剤として、一般式（１）
（式中のＲ１，ＲｔおよびＲ３は炭素数１〜４又は、■
２〜２２のアルキル基又は、ベンジル基、ＸはＣＩ、Ｂ
ｒ、Ｉを示す）で表されるグリシジルトリアルキルアン
モニウムハライドを使用することにより、極めて短時間
でカチオン化の反応率が上がり、しかもより容易に製造
できる方法を見いだし、本発明を完成するに至った。[Means for Solving the Problems] In order to develop a method for producing cationically modified starch that overcomes the drawbacks of the above-mentioned methods, the present inventors have conducted intensive research and have found that starch is dispersed in water and a catalyst is Potassium hydroxide was used as the cationizing agent, and general formula (1) (wherein R1, Rt and R3 have 1 to 4 carbon atoms or
2-22 alkyl group or benzyl group, X is CI, B
By using a glycidyl trialkylammonium halide represented by r, Ta.
即ち、本発明は、澱粉と一般式（１）
（式中のＲ、、Ｒ、およびＲ３は炭素数１〜４又は、１
２〜２２のアルキル基又は、ベンジル基、ＸはＣ１，Ｂ
ｒ、Ｉを示す）で表されるグリシジルトリアルキルアン
モニウムハライドとの反応によりカチオン変性澱粉を製
造する方法
において、溶媒に水を用い、触媒として水酸化カリウム
を用いて、０．５〜３時間という短時間で。That is, the present invention provides starch and general formula (1) (wherein R, , R, and R3 have 1 to 4 carbon atoms or 1
2-22 alkyl group or benzyl group, X is C1, B
In a method for producing cationically modified starch by reaction with glycidyl trialkylammonium halide represented by r, In a short time.
反応させることを特徴とするカチオン変性澱粉の製造方
法を提供するものである。The present invention provides a method for producing cationically modified starch, which is characterized by carrying out a reaction.
本発明の原料の澱粉としては、一般に使用されている澱
粉はすべて使用でき、例えば、トウモロコシ、ばれいし
ょ、タピオカ、などから得られるものを挙げることがで
きる。All commonly used starches can be used as the raw material starch of the present invention, including those obtained from corn, potato, tapioca, and the like.
本発明の方法は、まず澱粉を水に分散させ、グリシジル
トリアルキルアンモニウムハライドのカチオン化剤、水
酸化カリウムを添加し、反応温度４０〜６０℃で行われ
る。この際、触媒として水酸化ナトリウムを使用した場
合、４５℃以上の高温では、糊化が進行して後処理が困
難であったが、水酸化カリウムを用いることにより、高
温で反応しても、糊化がおこらず０．５〜３時間という
極めて短時間で、容易に製造することができる。In the method of the present invention, starch is first dispersed in water, a cationizing agent for glycidyltrialkylammonium halide and potassium hydroxide are added, and the reaction temperature is 40 to 60°C. At this time, when sodium hydroxide was used as a catalyst, gelatinization progressed at high temperatures of 45°C or higher, making post-treatment difficult; however, by using potassium hydroxide, even at high temperatures, It can be easily produced in an extremely short time of 0.5 to 3 hours without gelatinization.
反応に用いる水酸化カリウムは、澱粉のグルコース単位
当たり、０，０３〜０．４モルの範囲で添加するのが好
ましい。水酸化カリウムは、そのままあるいは、水溶液
として添加して用いる。溶媒である水は、乾燥澱粉１重
量部につき、１５〜４重量部、好ましくは１．８〜２３
重量部使用する。水かこの範囲より少なくなると、高粘
度スラリーを形成して、取り扱いが困難となる。また、
多くなると水酸化カリウム及びカチオン化剤との接触が
不十分となり、反応率が悪くなるという問題点を引き起
こす。Potassium hydroxide used in the reaction is preferably added in an amount of 0.03 to 0.4 mol per glucose unit of starch. Potassium hydroxide is used as it is or added as an aqueous solution. The amount of water as a solvent is 15 to 4 parts by weight, preferably 1.8 to 23 parts by weight, per 1 part by weight of dry starch.
Use parts by weight. When the amount of water is less than this range, a highly viscous slurry is formed and difficult to handle. Also,
If the amount increases, contact with potassium hydroxide and the cationizing agent becomes insufficient, causing a problem of poor reaction rate.
カチオン化剤の使用量は、所望の窒素含有率のものを得
るよう、用途に合わせ適宜決定される。The amount of the cationizing agent to be used is appropriately determined depending on the application so as to obtain the desired nitrogen content.
通常窒素含有率０．１〜４重量％でほとんどの用途を満
足し、この場合のカチオン化剤の使用量は、乾燥澱粉１
００重量部に対し、３．４〜４３．２重量部となる。Generally, a nitrogen content of 0.1 to 4% by weight satisfies most uses, and in this case the amount of cationizing agent used is 1% to 1% by weight of dry starch.
00 parts by weight, it becomes 3.4 to 43.2 parts by weight.
反応温度は、４０〜６０℃、好ましくは、５０〜５５℃
であり、反応時間としては０．５〜３時間で充分である
。このようにして得られた反応液を酸により中和し、反
応生成物を分離、精製し、減圧下で乾燥後製品とする。The reaction temperature is 40-60°C, preferably 50-55°C.
Therefore, a reaction time of 0.5 to 3 hours is sufficient. The reaction solution thus obtained is neutralized with an acid, the reaction product is separated and purified, and the product is obtained after drying under reduced pressure.
本発明によれば、カチオン化剤の反応率が上がリ、反応
時間も短縮でき、しかもより容易に製造することができ
る。 次に、本発明を実施例に基づき、更に、詳細に説
明する。According to the present invention, the reaction rate of the cationizing agent can be increased, the reaction time can be shortened, and production can be made easier. Next, the present invention will be explained in more detail based on examples.
［実施例１］
コーンスターチ８０ｇ（含水率１２．５％）を水１３０
ｇに分散させ、この分散液に有効成分２．４ｇ（対澱粉
０．０４倍モル：グルコース単位当たり以下同様）のグ
リシジルトリメチルアンモニウムクロライド（以下ＧＴ
Ａと略す）水溶液を添加し、その後、５重量％水酸化カ
リウム水溶液３８゜５ｇ（対澱粉０．０８倍モル）を加
えて昇温し、５５℃で１時間、撹拌した。この後、５重
量％塩酸水溶液を用いて中和した。次に２００ｇメタノ
ール中に反応液３０ｇを投入し、反応生成物を沈澱させ
、この沈澱物を３０分間、メタノール中で洗浄し、これ
を濾別した。このような洗浄精製を、２回繰り返した後
、反応生成物を減圧下で乾燥した。[Example 1] 80 g of cornstarch (water content 12.5%) was mixed with 130 g of water.
Glycidyltrimethylammonium chloride (hereinafter referred to as GT
A) aqueous solution was added, and then 38.5 g of a 5% by weight aqueous potassium hydroxide solution (0.08 times the mole of starch) was added, the temperature was raised, and the mixture was stirred at 55° C. for 1 hour. Thereafter, it was neutralized using a 5% by weight aqueous hydrochloric acid solution. Next, 30 g of the reaction solution was poured into 200 g of methanol to precipitate the reaction product, and this precipitate was washed in methanol for 30 minutes and filtered. After repeating such washing and purification twice, the reaction product was dried under reduced pressure.
このようにして得られたカチオン変性澱粉は、窒素含有
率が０２２２重量％であった。この窒素含有率より、澱
粉に対するＧＴＡの反応率は、６０％であった。The cationically modified starch thus obtained had a nitrogen content of 0.222% by weight. Based on this nitrogen content, the reaction rate of GTA to starch was 60%.
［実施例２〜３１
第１表に示した反応条件で実施例１と同様の方法により
、カチオン変性澱分を得た。このようにして得られた生
成物の窒素含有率、ＧＴＡの反応率を同じく第１表に示
した。Examples 2 to 31 Cation-modified precipitates were obtained in the same manner as in Example 1 under the reaction conditions shown in Table 1. The nitrogen content and GTA reaction rate of the product thus obtained are also shown in Table 1.
［比較例１］
コーンスターチ８０ｇ（含水率１２．５％）を水１３０
ｇに分散させ、この分散液に有効成分２４ｇ（澱分０．
０４倍モル）のＧＴＡ水溶液を添加し、５重量％水酸化
ナトリウム水溶液２５．３ｇ（対澱粉０．０８倍モル）
を加えて昇温し、４５℃（４５℃以上では澱粉が、高粘
度化する）で１時間撹拌した。この後、５重量％塩酸水
溶液を用いて中和した。次に２００ｇメタノール中に反
応液３０ｇを投入し、反応生成物を沈澱させ、この沈澱
物を３９分間、メタノール中で、洗浄し、これを濾別し
た。このような洗浄精製を２回繰り返した後、反応生成
物を減圧下で乾燥した。[Comparative Example 1] 80 g of corn starch (water content 12.5%) and 130 g of water
24 g of the active ingredient (0.g of lees) is added to this dispersion.
04 times mole) of GTA aqueous solution was added, and 25.3 g of 5% by weight sodium hydroxide aqueous solution (0.08 times mole of starch) was added.
was added, the temperature was raised, and the mixture was stirred for 1 hour at 45°C (starch becomes highly viscous at temperatures above 45°C). Thereafter, it was neutralized using a 5% by weight aqueous hydrochloric acid solution. Next, 30 g of the reaction solution was poured into 200 g of methanol to precipitate the reaction product, and this precipitate was washed in methanol for 39 minutes and filtered. After repeating such washing and purification twice, the reaction product was dried under reduced pressure.
このようにして、得られたカチオン変性澱粉は、窒素含
有率０．’＋ ７１重量％であった。この窒素含有率よ
り、澱粉に対するＧＴＡの反応率は４３％であった。The cationically modified starch thus obtained has a nitrogen content of 0. '+71% by weight. Based on this nitrogen content, the reaction rate of GTA to starch was 43%.
［比較例２〜３１
第１表に示した反応条件で比較例Ｉと同様の方法より、
カチオン変性澱分を得た。このようにして得られた生成
物の窒素含有率、ＧＴＡ反応率を同様に第１表に示した
。[Comparative Examples 2 to 31] By the same method as Comparative Example I under the reaction conditions shown in Table 1,
A cationically modified sludge was obtained. The nitrogen content and GTA reaction rate of the product thus obtained are also shown in Table 1.
（比較例４〜６コ
コーンスターチ８０ｇ（含水率１２．５％）を水１３０
ｇに分散させ、この分散液に有効成分２゜９ｇ（対澱粉
０．０４倍モル）の３−クロロ２ヒドロキンプロピルト
リメチルアンモニウムクロライド（以下ＨＴＡと略す）
水溶液を添加し、その後、５重量％水酸化カリウム水溶
液５３．９ｇ（対澱粉０１２倍モル）を加えて昇温し、
５５℃で撹拌した。その後の操作は、比較例１と同様の
方法で行いカチオン変性澱粉を得た。反応条件、及び窒
素含有率、ＨＴＡの反応率を第１表に示した。(Comparative Examples 4 to 6 80 g of cocorn starch (water content 12.5%) was added to 130 g of water.
2.9 g of the active ingredient (0.04 times the mole of starch) of 3-chloro2hydroquinepropyltrimethylammonium chloride (hereinafter abbreviated as HTA) was added to this dispersion.
Add an aqueous solution, then add 53.9 g of a 5% by weight aqueous potassium hydroxide solution (012 times the mole of starch) and raise the temperature.
Stir at 55°C. The subsequent operations were performed in the same manner as in Comparative Example 1 to obtain cationically modified starch. The reaction conditions, nitrogen content, and HTA reaction rate are shown in Table 1.
［発明の効果］
以上のように、本発明による製造方法は、簡単な操作の
もと、極めて短時間で、かつ高反応率で、カチオン変成
澱粉を得ることかできる優れた方法である。[Effects of the Invention] As described above, the production method according to the present invention is an excellent method that allows cationically modified starch to be obtained with simple operations, in an extremely short period of time, and at a high reaction rate.
Claims (1)
は、１２〜２２のアルキル基又は、ベンジル基、ＸはＣ
ｌ、Ｂｒ、Ｉを示す） で表されるグリシジルトリアルキルアンモニウムハライ
ドとを、水溶媒中スラリー状態で反応させ、カチオン変
性澱粉とする製造方法において、触媒として水酸化カリ
ウムを用いることを特徴とするカチオン変性澱粉の製造
方法。[Claims] Starch and the general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R_1, R_2 and R_3 are alkyl groups having 1 to 4 carbon atoms or 12 to 22 carbon atoms. Or benzyl group, X is C
1, Br, I) in a slurry state in an aqueous solvent to produce a cationically modified starch, characterized in that potassium hydroxide is used as a catalyst. A method for producing cationically modified starch.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2026562A JPH03229701A (en) | 1990-02-05 | 1990-02-05 | Production of cation-modified starch |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2026562A JPH03229701A (en) | 1990-02-05 | 1990-02-05 | Production of cation-modified starch |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03229701A true JPH03229701A (en) | 1991-10-11 |
Family
ID=12196977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2026562A Pending JPH03229701A (en) | 1990-02-05 | 1990-02-05 | Production of cation-modified starch |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03229701A (en) |
-
1990
- 1990-02-05 JP JP2026562A patent/JPH03229701A/en active Pending
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