WO2019064633A1 - Procédé de fabrication de carboxyméthylcellulose ou de sel de celle-ci - Google Patents

Procédé de fabrication de carboxyméthylcellulose ou de sel de celle-ci Download PDF

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Publication number
WO2019064633A1
WO2019064633A1 PCT/JP2018/008545 JP2018008545W WO2019064633A1 WO 2019064633 A1 WO2019064633 A1 WO 2019064633A1 JP 2018008545 W JP2018008545 W JP 2018008545W WO 2019064633 A1 WO2019064633 A1 WO 2019064633A1
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Prior art keywords
alkali
mol
cellulose
less
salt
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PCT/JP2018/008545
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English (en)
Japanese (ja)
Inventor
亮 角張
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第一工業製薬株式会社
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Publication of WO2019064633A1 publication Critical patent/WO2019064633A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/02—Alkyl or cycloalkyl ethers
    • C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
    • C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
    • C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/02—Oxycellulose; Hydrocellulose; Cellulosehydrate, e.g. microcrystalline cellulose
    • C08B15/04—Carboxycellulose, e.g. prepared by oxidation with nitrogen dioxide

Definitions

  • the present invention relates to a method for producing carboxymethylcellulose or a salt thereof.
  • carboxymethyl cellulose or a salt thereof is produced by performing an alkali cellulose conversion reaction in which cellulose is reacted with an alkali, and then adding an etherifying agent to the obtained alkali cellulose to perform an etherification reaction.
  • an alkali cellulose conversion reaction in which cellulose is reacted with an alkali
  • an etherifying agent for example, after performing an alkali cellulose conversion reaction using a mixed solvent containing water and an organic solvent, monochloroacetic acid is added to perform an etherification reaction, and thereafter, after excess alkali is neutralized with an acid, the mixed solvent is removed.
  • the carboxymethylcellulose or the salt thereof produced by the production method described in Patent Document 1 described above did not have sufficient storage stability for a long time.
  • An object of the present invention is to provide a method for producing carboxymethyl cellulose or a salt thereof which is excellent in storage stability and in which the decrease in viscosity is small for a long time such as 1 year to 2 years.
  • an alkali cellulose conversion step in which cellulose and an alkali are reacted in the presence of a mixed solvent containing water and an organic solvent, the alkali cellulose obtained in the above step 1 and
  • the method includes an etherification step (step 2) of reacting with an etherifying agent, and a purification step (step 3) of washing and drying the reaction mixture obtained in step 2; 2.0 mol or more and 2.5 mol or less of alkali and 10 mol or more and 15 mol or less of water are used per 1 mol of glucose unit, and the concentration of the alkali to water is 0.5 mol% or more and 1.0 mol% or less
  • the above step 1 is carried out at a reaction time of 60 minutes to 120 minutes under conditions of pH 9 to 14 and a reaction temperature of 5 ° C. to 30 ° C.
  • the step 3 includes a pH adjusting step, and the reaction mixture is adjusted to pH 9 or more and 14 or less in the pH adjusting step.
  • the method for producing carboxymethylcellulose or a salt thereof includes the following steps 1 to 3.
  • Alkaline cellulose conversion step (step 1) in which cellulose and alkali are reacted in the presence of a mixed solvent containing water and an organic solvent
  • Step 1 Alkali cellulose conversion process
  • the cellulose is not particularly limited, and examples thereof include ground pulp, wood pulp, cotton linter pulp, waste paper pulp and the like. These raw material celluloses may be used alone or in combination of two or more.
  • alkali examples include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and any one kind or two or more kinds can be used in combination.
  • the amount of alkali used is 2.0 moles or more and 2.5 moles or less of alkali per 1 mole of anhydroglucose unit constituting cellulose. Preferably it is 2.1 mol or more and 2.4 mol or less. If it is in the said range, carboxymethylcellulose or its salt excellent in long-term storage stability can be obtained.
  • a mixed solvent containing water and an organic solvent is used as a solvent for performing the alkali cellulose conversion reaction.
  • the content of the organic solvent with respect to 100 parts by mass of water is 160 parts by mass or more and 500 parts by mass or less, preferably 200 parts by mass or more and 400 parts by mass or less.
  • the amount of water used relative to cellulose in the mixed solvent is 10 mol or more and 15 mol or less per 1 mol of anhydroglucose unit constituting the cellulose. Preferably, it is 11 to 13 moles.
  • organic solvent examples include alcohol solvents such as ethyl alcohol, methyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol and isobutyl alcohol, ketone solvents such as acetone, diethyl ketone and methyl ethyl ketone, dioxane, diethyl ether, etc. It can be mentioned. These may be used alone or as a mixture of two or more. Among these, monohydric alcohols having 1 to 4 carbon atoms are preferable, and monohydric alcohols having 1 to 3 carbon atoms are more preferable, because of their excellent compatibility with water.
  • alcohol solvents such as ethyl alcohol, methyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol and isobutyl alcohol
  • ketone solvents such as acetone, diethyl ketone and methyl ethyl ketone, dioxane, diethyl
  • the content of the organic solvent is preferably 20% by mass or more and 70% by mass or less, and is 30% by mass or more and 60% by mass or less in the reaction liquid (the entire reaction liquid containing cellulose, alkali and mixed solvent) More preferable.
  • the concentration of alkali to water is preferably 0.5 mol% or more and 1.0 mol% or less.
  • the concentration of alkali to water is more preferably 0.6 mol% or more and 0.8 mol% or less.
  • Proportion of organic solvent and cellulose It is preferable to use 250 parts by mass or more and 1000 parts by mass or less of the organic solvent with respect to 100 parts by mass of cellulose. By setting it as the said range, carboxymethylcellulose or its salt excellent in long-term storage stability can be obtained.
  • the lower limit of the content of the organic solvent is more preferably 350 parts by mass or more, and the upper limit is more preferably 700 parts by mass or less.
  • alkali cellulose conversion reaction (Conditions of alkaline cellulose reaction)
  • the uniformity of the reaction is enhanced and carboxymethyl cellulose excellent in long-term storage stability or The salt can be obtained.
  • the pH is 9 or more, which allows the alkali cellulose reaction to proceed.
  • the pH is preferably 11 or more, more preferably 12 or more.
  • the upper limit of pH is 14 or less, preferably 13.5 or less.
  • the reaction temperature is 5 ° C. or more and 30 ° C. or less, the lower limit is more preferably 20 ° C. or more, and the upper limit is more preferably 28 ° C. or less.
  • the reaction time is 60 minutes or more and 120 minutes or less, more preferably 800 minutes or more and 100 minutes or less.
  • the alkali cellulose conversion process can be performed using a reactor capable of mixing and stirring the above-mentioned components while controlling the temperature, and various reactors conventionally used for the alkali cellulose conversion reaction may be used. Can.
  • Step 2 Etherification Step
  • an etherifying agent is added to carry out an etherification reaction to complete the carboxymethylation reaction.
  • the etherifying agent monochloroacetic acid, sodium monochloroacetate, methyl monochloroacetate, ethyl monochloroacetate, isopropyl monochloroacetate and the like can be mentioned.
  • the lower limit of the ratio of the etherifying agent to 1 mol of glucose unit is preferably 0.6 mol or more, more preferably 0.7 mol or more, and the upper limit is more preferably 1.3 mol or less, still more preferably It is 1.1 mol or less.
  • the mixing of the solution containing the alkali cellulose and the etherifying agent is preferably carried out in a plurality of times or by dropwise addition to prevent the reaction mixture from becoming hot.
  • the temperature of the reaction mixture during mixing is preferably 30 ° C. or more and 80 ° C. or less.
  • the reaction temperature after completion of the mixing is not particularly limited, but is preferably 60 ° C. or more and 100 ° C. or less. With such a range, long-term storage stability can be further improved.
  • the lower limit of the reaction temperature is more preferably 70 ° C. or more, and the upper limit is more preferably 90 ° C. or less.
  • the reaction time after completion of the mixing is not particularly limited, but is preferably 10 minutes or more and 90 minutes or less. With such a range, long-term storage stability can be further improved.
  • the lower limit of the reaction time is more preferably 20 minutes or more, and the upper limit is more preferably 80 minutes or less.
  • the etherification step may be carried out using the reactor used for the alkali cellulose conversion reaction as it is, or alternatively, using another reactor capable of mixing and stirring the above components while controlling the temperature. You may go.
  • the purification step is a step of washing and drying the reaction mixture obtained in the above step 2, and may include, as one embodiment, a solvent removal step, a washing step and a drying step, and also prior to the solvent removal step. It may further include a pH adjustment step.
  • the purification step is a step of removing the mixed solvent from the reaction mixture using the reaction mixture having a pH of 9 or more and 14 or less after completion of the above-mentioned etherification reaction, followed by washing and drying. It is also good.
  • a pH adjustment step is a step of removing the mixed solvent from the reaction mixture using the reaction mixture having a pH of 9 or more and 14 or less after completion of the above-mentioned etherification reaction, followed by washing and drying. It is also good.
  • the pH adjustment step is a step of adjusting the pH of the reaction mixture to 9 or more and 11 or less by adding an acid after completion of the above-mentioned etherification reaction, and a part of the excess alkali remaining is neutralized with the acid.
  • the pH adjustment step is basically performed when the pH of the reaction mixture after completion of the etherification reaction is larger than the above range, but may be performed when it is within the above range (for example, the pH is In the case of 11 or less, it is about 9.5, etc.).
  • the reaction mixture may be cooled, for example, to a temperature of 60 ° C. or less.
  • the acid may be, for example, an organic acid such as formic acid, acetic acid, propionic acid, malic acid, citric acid and sulfamic acid, or an inorganic acid such as hydrochloric acid, nitric acid and sulfuric acid.
  • an organic acid such as formic acid, acetic acid, propionic acid, malic acid, citric acid and sulfamic acid
  • an inorganic acid such as hydrochloric acid, nitric acid and sulfuric acid.
  • the solvent removal step is a step of removing a mixed solvent containing water and an organic solvent, for example, by filtration, distillation under reduced pressure, or a combination thereof.
  • the content of the mixed solvent in the reaction mixture after solvent removal is not particularly limited, and may be, for example, 70% by mass or less, or 60% by mass or less. Moreover, you may remove until content of a mixed solvent will be 5 mass% or less using a kneading machine etc.
  • an alkali is added to the reaction mixture after removing the solvent (hereinafter referred to as crude carboxymethylcellulose salt), and the pH is adjusted to within the range of 9 or more and 11 or less (more preferably 9.5 or more and 11 or less). It is also good.
  • the alkali in this case the same alkali as the alkali used in step 1 can be used.
  • washing step a mixed solvent of water and an organic solvent can be used, and the crude carboxymethylcellulose salt is washed with the mixed solvent.
  • the mixed solvent the same one as in step 1 can be used, and as the organic solvent, a monohydric alcohol having 1 to 4 carbon atoms is more preferable.
  • the drying step is a step of drying the washed crude carboxymethylcellulose salt, and examples of the drying method include air drying, heat drying, reduced pressure drying, reduced pressure heat drying and the like.
  • Step 4 Grinding Process
  • the grinding step is a step of grinding the purified product obtained in the above step 3.
  • a dry pulverizer may be used or a wet pulverizer may be used.
  • various pulverizers described below may be used alone or two or more kinds of them may be combined to carry out a pulverizing treatment of two or more stages, and further, two stages with the same model. The above-mentioned pulverizing treatment may be carried out.
  • mesh mill made by Horai
  • Atoms made by Yamamoto Hyakuma Seisakusho
  • knife mill made by Pulman
  • granulator made by Helbolt
  • rotary cutter mill made by Nara Machinery Co., Ltd.
  • Pulperizer, Fine Impact Mill, Super Micron Mill manufactured by Hosokawa Micron Corporation
  • Sample Mill Bantam Mill
  • Atomizer manufactured by Seishin Co., Ltd.
  • Tornado Mill manufactured by Nikkiso Co., Ltd.
  • Turbo Mill manufactured by Turbo Industries, Ltd.
  • Bevel Impactor manufactured by Aikawa Iron Works Co., Ltd.
  • CGS type jet mill manufactured by Mitsui Mining Co., Ltd.
  • jet mill manufactured by Mitaka Industrie Co., Ltd.
  • Ebara jet micronizer manufactured by Ebara Corp.
  • selenium mirror manufactured by Masuko Sangyo Co., Ltd.
  • supersonic speed Jet mill manufactured by Nippon Pneumatic Mfg. Co., Ltd.
  • a mass colloider manufactured by Masuko Sangyo Co., Ltd.
  • a high pressure homogenizer manufactured by Sanmaru Kikai Kogyo Co., Ltd.
  • a bead mill manufactured by Imex Co., Ltd.
  • the ground carboxymethylcellulose or its salt can be further classified.
  • the classification method include a method using a sieve, and a method using a classifier such as a cyclone classifier.
  • the measuring method of each physical property is based on the following method.
  • A (af-bf 1) / weight of dry matter (g)
  • Viscosity retention rate After the viscosity measured above has passed a predetermined period (1 month, 3 months, 6 months, 12 months, 18 months, 24 months) at 25 ° C. at V 0 (mPa ⁇ s), the above The viscosity of a 1% by mass aqueous solution prepared by the method of (3) and measured was V n (mPa ⁇ s), and the calculation was performed according to the following formula (2).
  • Viscosity retention (%) V n (mPa ⁇ s) / V 0 (mPa ⁇ s) ⁇ 100 (Equation 2)
  • the reaction solution obtained is cooled to 60 ° C. and adjusted to pH 9.5 using a 50 mass% aqueous acetic acid solution, and then the reaction solvent is evaporated and recovered using a vacuum filter to obtain crude carboxymethylcellulose sodium salt (nonvolatile (40% by mass) was obtained.
  • the crude carboxymethylcellulose sodium salt obtained was adjusted to pH 9.5 by adding sodium hydroxide.
  • the obtained dried product was pulverized using an impact type mill (Pulperizer manufactured by Hosokawa Micron Corporation), and classified with a standard sieve of 83 mesh to obtain a carboxymethylcellulose sodium salt.
  • Examples 2 to 9, Comparative Examples 1 to 4 It manufactured similarly to Example 1 except having changed the quantity of the solvent and 50 mass% sodium hydroxide aqueous solution in alkali-cellulose reaction into the quantity shown in Table 1, and obtained carboxymethylcellulose sodium salt.
  • ком ⁇ онент such as detergent compositions such as shampoos and rinses, treatments and conditioners, cosmetic compositions such as emulsions and creams, softener compositions for clothes, etc., and also polymer active agents and dispersions It can be used in a wide range of fields as an agent, an emulsifier, a modifier, a coagulant, a viscosity modifier and the like.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

L'invention fournit le procédé de fabrication d'une carboxyméthylcellulose ou d'un sel de celle-ci, laquelle carboxyméthylcellulose présente une faible baisse de viscosité sur le long terme, et est dotée d'une excellente stabilité de conservation. Le procédé de fabrication de l'invention inclut : une étape de transformation en alcali-cellulose (étape 1) au cours de laquelle une cellulose et un alcali sont mis en réaction en présence d'un solvant mixte contenant une eau et un solvant organique ; une étape d'éthérification (étape 2) au cours de laquelle l'alcali-cellulose obtenue lors de ladite étape 1 est mis en réaction avec un agent d'éthérification ; une étape de purification (étape 3) au cours de laquelle le mélange réactionnel obtenu lors de ladite étape 2 est nettoyé et séché ; et une étape de broyage (étape 4) au cours de laquelle le produit purifié obtenu lors de ladite étape 3 est broyé. Ladite étape 1 met en œuvre un alcali à raison de 2,0 moles ou plus à 2,5 moles ou moins, et une eau à raison de 10 moles ou plus à 15 moles ou moins pour 1 mole d'unité d'anhydroglucose configurant la cellulose. La concentration en alcali par rapport à l'eau, est supérieure ou égale à 0,5% en moles et inférieure ou égale à 1,0% en moles.
PCT/JP2018/008545 2017-09-27 2018-03-06 Procédé de fabrication de carboxyméthylcellulose ou de sel de celle-ci WO2019064633A1 (fr)

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JP2017186155A JP2019059856A (ja) 2017-09-27 2017-09-27 カルボキシメチルセルロースまたはその塩の製造方法

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022162133A1 (fr) 2021-01-29 2022-08-04 Nutrition & Biosciences Usa 1, Llc Procédé de préparation de carboxyméthylcellulose ayant une stabilité au stockage améliorée

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JPS5975903A (ja) * 1982-09-30 1984-04-28 ヘキスト・アクチエンゲゼルシヤフト 水溶性ナトリウムカルボキシメチルセルロ−スの製造方法
JPH10158301A (ja) * 1996-11-29 1998-06-16 Nippon Paper Ind Co Ltd 耐薬品性に優れたカルボキシメチルセルロースエーテルアルカリ塩
JP2003183301A (ja) * 2001-12-21 2003-07-03 Dai Ichi Kogyo Seiyaku Co Ltd カルボキシメチルセルロース塩の製造法
JP2004182932A (ja) * 2002-12-05 2004-07-02 Dai Ichi Kogyo Seiyaku Co Ltd 低曳糸性カルボキシメチルセルロース塩の製造法
JP2008019344A (ja) * 2006-07-13 2008-01-31 Dai Ichi Kogyo Seiyaku Co Ltd 部分酸型カルボキシメチルセルロースの製造方法
JP2008222859A (ja) * 2007-03-13 2008-09-25 Dai Ichi Kogyo Seiyaku Co Ltd 高い降伏値を有するカルボキシメチルセルロースナトリウム塩の製造方法
JP2013523919A (ja) * 2010-03-30 2013-06-17 ダウ グローバル テクノロジーズ エルエルシー 新規な高粘度カルボキシメチルセルロースおよび製造方法
WO2016031449A1 (fr) * 2014-08-28 2016-03-03 第一工業製薬株式会社 Procédé de fabrication de sel de carboxyméthyl cellulose pour électrodes de batteries secondaires à électrolyte non aqueux, électrode pour batteries secondaires à électrolyte non aqueux et batterie secondaire à électrolyte non aqueux
JP2016069589A (ja) * 2014-10-01 2016-05-09 第一工業製薬株式会社 セルロースナノファイバー水分散体の製造方法
WO2017145904A1 (fr) * 2016-02-26 2017-08-31 第一工業製薬株式会社 Procédé de préparation de carboxyméthylcellulose ou d'un sel de celle-ci, et liant pour électrode

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Publication number Priority date Publication date Assignee Title
JPS5975903A (ja) * 1982-09-30 1984-04-28 ヘキスト・アクチエンゲゼルシヤフト 水溶性ナトリウムカルボキシメチルセルロ−スの製造方法
JPH10158301A (ja) * 1996-11-29 1998-06-16 Nippon Paper Ind Co Ltd 耐薬品性に優れたカルボキシメチルセルロースエーテルアルカリ塩
JP2003183301A (ja) * 2001-12-21 2003-07-03 Dai Ichi Kogyo Seiyaku Co Ltd カルボキシメチルセルロース塩の製造法
JP2004182932A (ja) * 2002-12-05 2004-07-02 Dai Ichi Kogyo Seiyaku Co Ltd 低曳糸性カルボキシメチルセルロース塩の製造法
JP2008019344A (ja) * 2006-07-13 2008-01-31 Dai Ichi Kogyo Seiyaku Co Ltd 部分酸型カルボキシメチルセルロースの製造方法
JP2008222859A (ja) * 2007-03-13 2008-09-25 Dai Ichi Kogyo Seiyaku Co Ltd 高い降伏値を有するカルボキシメチルセルロースナトリウム塩の製造方法
JP2013523919A (ja) * 2010-03-30 2013-06-17 ダウ グローバル テクノロジーズ エルエルシー 新規な高粘度カルボキシメチルセルロースおよび製造方法
WO2016031449A1 (fr) * 2014-08-28 2016-03-03 第一工業製薬株式会社 Procédé de fabrication de sel de carboxyméthyl cellulose pour électrodes de batteries secondaires à électrolyte non aqueux, électrode pour batteries secondaires à électrolyte non aqueux et batterie secondaire à électrolyte non aqueux
JP2016069589A (ja) * 2014-10-01 2016-05-09 第一工業製薬株式会社 セルロースナノファイバー水分散体の製造方法
WO2017145904A1 (fr) * 2016-02-26 2017-08-31 第一工業製薬株式会社 Procédé de préparation de carboxyméthylcellulose ou d'un sel de celle-ci, et liant pour électrode

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022162133A1 (fr) 2021-01-29 2022-08-04 Nutrition & Biosciences Usa 1, Llc Procédé de préparation de carboxyméthylcellulose ayant une stabilité au stockage améliorée

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