WO2015064512A1 - Épaississant - Google Patents

Épaississant Download PDF

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Publication number
WO2015064512A1
WO2015064512A1 PCT/JP2014/078422 JP2014078422W WO2015064512A1 WO 2015064512 A1 WO2015064512 A1 WO 2015064512A1 JP 2014078422 W JP2014078422 W JP 2014078422W WO 2015064512 A1 WO2015064512 A1 WO 2015064512A1
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WIPO (PCT)
Prior art keywords
polymer compound
weight
percent
extraction
thickener
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Application number
PCT/JP2014/078422
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English (en)
Inventor
Naotaka Nishio
Takashi Arai
Shuji Yoshioka
Koichi SUHARA
Original Assignee
Daicel Corporation
Toyota Tsusho Corporation
Priority date (The priority date 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 date listed.)
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Application filed by Daicel Corporation, Toyota Tsusho Corporation filed Critical Daicel Corporation
Publication of WO2015064512A1 publication Critical patent/WO2015064512A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H8/00—Macromolecular compounds derived from lignocellulosic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/14—Hemicellulose; Derivatives thereof

Definitions

  • the present invention relates to a polymer compound (macromolecular compound) available from at least one of Corchorus capsularis L. and Corchorus aestuans L.
  • the polymer compound is advantageously usable as a thickener for fossil resource extraction.
  • excavation is performed horizontally along a formation including a fossil resource.
  • a high-viscosity liquid containing water, a granular proppant such as sand grains, and chemical substances of various kinds is injected into the resulting borehole to cause fractures in the formation.
  • the granular proppant is allowed to slip into the formed fractures to prevent the fractures from closing naturally, and thus the target fossil resource is continuously
  • the chemical substances for use herein include chemicals such as acids, antiseptic agents, and friction reducers; and, in combination with them, a thickener so as to allow the granular proppant to disperse stably.
  • CMC carboxymethylcellulose
  • the guar gum suffers from competition in demand between the novel use (fossil resource extraction use) and already- existing uses (e.g., food or food additive uses).
  • the CMC has poor salt tolerance and has a sharply decreasing viscosity in the presence of a salt.
  • JP-A Japanese Unexamined Patent Application Publication No. 2012-167273
  • NPL 1 Bulletin of Industrial Research Division, Mie Prefectural Science and Technology Promotion Center, No. 29 (2005)
  • an object of the present invention is to provide a polymer compound that is available from a plant as a raw material, can be easily extracted from the raw
  • Another object of the present invention is to provide a thickener for fossil resource extraction, including the polymer compound.
  • Yet another object of the present invention is to provide a fluid for fossil resource extraction, including the thickener for fossil resource extraction.
  • Corchorus capsularis L. and Corchorus aestuans L. contain large amounts of polymer compounds.
  • Corchorus capsularis L. and Corchorus aestuans L. are used as fibers as raw materials typically for fabrics, but leaves of these plants have been disposed as wastes and are thereby easily available.
  • Polymer compounds extracted from the leaves of Corchorus capsularis L. and/or Corchorus aestuans L. have different viscosities depending on extraction conditions, and a polymer compound having a high viscosity can be obtained under a specific condition.
  • the polymer compound can stably maintain a
  • the present invention has been made based on these findings .
  • the present invention provides, in a first aspect, a polymer compound extracted from at least one of Corchorus capsularis L. and Corchorus aestuans L.
  • the polymer compound has a shear viscosity of 0.2 Pa -s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an aqueous solution containing 1 percent by weight of the polymer compound.
  • the polymer compound may have a shear viscosity of 0.2 Pa -s or more at a temperature of 25°C and a shear rate of 10
  • the polymer compound may have a solubility of 1 g or more per 100 g of water at a temperature of 25°C.
  • the present invention provides, in a second aspect, a thickener for fossil resource extraction.
  • the thickener includes the polymer compound.
  • the present invention provides, in a third aspect, a fluid for fossil resource extraction.
  • the fluid includes the thickener for fossil resource extraction.
  • the present invention relates to
  • the present invention relates to the polymer compound extracted from at least one of Corchorus capsularis L. and Corchorus aestuans L.
  • the polymer compound has a shear viscosity of 0.2 Pa-s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an aqueous solution
  • the polymer compound according to [1] may have a shear viscosity of 0.2 Pa -s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an aqueous solution
  • the polymer compound according to [1] may have a shear viscosity of 0.2 Pa-s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an aqueous solution
  • the polymer compound according to any one of [1] to [3] may have a solubility of 1 g or more per 100 g of water at a temperature of 25°C and a pH of 7.0.
  • the present invention also relates to the thickener for fossil resource extraction.
  • the thickener includes the polymer compound according to any one of [1] to [4] .
  • the thickener for fossil resource extraction according to [5] may contain the polymer compound in a content of 60 percent by weight or more based on the total amount of the thickener.
  • the present invention further relates to the fluid for fossil resource extraction.
  • the fluid includes the thickener for fossil resource extraction according to [5] or [6] .
  • the fluid for fossil resource extraction according to [7] may contain the thickener in a content from 0.01 to 5 percent by weight based on the total amount of the fluid.
  • the fluid for fossil resource extraction according to [7] ⁇ or [8] may contain the polymer compound according to any one of [1] to [4] in a content from 0.01 to 5 percent by weight based on the total amount of the fluid.
  • the fluid for fossil resource extraction according to any one of [7] to [9] may include water, a granular proppant, and the thickener for fossil resource extraction.
  • the present invention also relates to a method for extracting a fossil resource.
  • the method uses the fluid for fossil resource extraction according to any one of [7] to [10] .
  • the polymer compound according to the present invention has a high viscosity and exhibits a more excellent
  • the guar gum suffers from competition in demand between the novel use (fossil resource extraction use) and already- existing uses (e.g., food or food additive uses) .
  • the polymer compound according to the present invention can employ leaves of Corchorus capsularis L.
  • the polymer compound is advantageous in availability of the raw material and can be produced from the raw material by a simple method.
  • the polymer compound can therefore be inexpensively and stably provided.
  • the polymer compound according to the present invention is highly biodegradable and loads a small burden on the environment. This significantly reduces the risk of pollution to drinking water even when the polymer compound leaks out into the ground.
  • the polymer compound has excellent salt tolerance and can continuously and stably exhibit a thickening effect even in the presence of a salt.
  • the polymer compound according to the present invention is therefore usable, instead of the guar gum and CMC, as a thickener typically for foodstuffs, cosmetics,
  • Fig. 1 is a graph indicating the shear viscosities (at 25°C) of polymer compounds obtained in examples and comparative examples each in a slurry
  • Fig. 2 is a graph indicating the shear
  • Fig. 3 is a chart indicating the result of proton nuclear magnetic resonance spectroscopy ( 1 H-NMR) of the polymer compound obtained in Example 1.
  • Fig. 4 is a chart indicating the result of infrared (IR) analysis of the polymer compound obtained in Example 1.
  • Fig. 5 is a chart indicating the result of thermogravimetry-differential thermal analysis (TG-DTA) of the polymer compound obtained in Example 1.
  • the polymer compound according to the present invention is prepared from at least one of Corchorus capsularis L. and Corchorus aestuans L. as a raw material.
  • Corchorus capsularis L. is an annual plant, is mainly produced in districts including India, Bangladesh, and other tropical zones, and has a scientific name of Corchorus capsularis L.
  • Corchorus aestuans L. is an annual plant, is originated typically from India and Egypt, and has a scientific name of Corchorus aestuans L. All portions, such as stems and leaves, of these plants can be used without limitation. Among them, the leaves are
  • Corchorus capsularis L. and Corchorus aestuans L. may be used in any form without limitation, such as a fresh one, dried one, or one after being subjected to a heat treatment typically by roasting.
  • the raw material for use herein is preferably fresh one, or dried one after drying at a low temperature of 50 °C or lower. This may allow the polymer compound to have a more excellent thickening effect.
  • the polymer compound according to the present invention is a hemicellulose extracted from cell-wall polysaccharides of at least one of Corchorus capsularis L. and Corchorus aestuans L. and is a polysaccharide containing at least a constitutional unit derived from a uronic acid. Part or all of acidic groups (carboxy groups) of the polysaccharide may form a salt.
  • such polymer compounds according to the present invention include a polysaccharide containing at least a constitutional unit derived from a uronic acid; and a compound corresponding to the polysaccharide, except with part or all of acidic groups (carboxy groups) of the polysaccharide forming a salt.
  • the polymer compound according to the present invention is highly soluble in water and has a solubility in water of 1 g or more, and preferably 3 g or more, per 100 g of water at a temperature of 25 °C and a pH of 7.0.
  • the polymer compound is therefore advantageously usable as a thickener for an aqueous composition.
  • the polymer compound according to the present invention has a shear viscosity of 0.2 Pa-s or more, preferably 0.3 Pa -s or more, more preferably 0.4 Pa-s or more, particularly preferably 0.5 Pa-s or more, and most preferably 0.55 Pa-s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an aqueous solution containing 1 percent by weight of the polymer compound.
  • the upper limit of the shear viscosity is typically 3 Pa-s and preferably 2 Pa-s.
  • the polymer compound according to the present invention therefore exhibits an excellent thickening effect.
  • the term "shear viscosity" as used herein refers to a value measured by a method described in the examples (working examples) .
  • Regular electrolyte polymer compounds such as CMC
  • CMC Regular electrolyte polymer compounds
  • a salt such as sodium chloride (NaCl) or another alkali metal halide
  • the polymer compound according to the present invention has excellent salt tolerance and has a shear viscosity of 0.2 Pa-s or more, preferably 0.4 Pa -s or more, and particularly preferably 0.5 Pa-s or more at a temperature of 25°C and a shear rate of 10 (1/s) in an agueous solution containing 10 percent by weight of a salt such as an alkali metal halide and 1 percent by weight of the polymer compound.
  • the shear viscosity is a shear viscosity in a salt-containing agueous solution containing 10 percent by weight of a salt (such as NaCl or another alkali metal halide) at a temperature of 25 °C and a shear rate of 10 (1/s).
  • a salt such as NaCl or another alkali metal halide
  • the solution is prepared by adding the salt to an aqueous solution containing 1 percent by weight of the polymer compound according to the present invention.
  • the upper limit of the shear viscosity is typically 3 Pa-s, and preferably 2 Pa-s.
  • the polymer compound according to the present invention has not a decreased viscosity but rather an increased viscosity in an aqueous solution containing the polymer compound in a
  • the polymer compound according to the present invention is a plant-derived component, is highly biodegradable, and is eventually degraded to carbon dioxide and water by microorganisms in the natural world.
  • polymer compound therefore loads a small burden on the environment and is highly safe.
  • the polymer compound according to the present invention may be produced typically through Step 1 of alkaline
  • the alkaline extraction in Step 1 may be performed by immersing the raw material in an alkaline aqueous solution.
  • the immersion in an alkaline aqueous solution allows cell walls of Corchorus capsularis L. and/or Corchorus aestuans L. to swell and enables efficient extraction of a polymer compound having an excellent thickening effect.
  • the alkaline aqueous solution is exemplified by aqueous
  • the alkaline aqueous solution for use in the extraction may have a pH of typically from about 8 to about 14, preferably from 9 to less than 13.5, particularly preferably from 9 to 13, and most preferably from 10 to 13.
  • the alkaline aqueous solution for use in the extraction if having a pH greater than the range, may tend to cause the extracted polymer compound to decompose, to thereby have a lower molecular weight, and to have a lower thickening effect.
  • the alkaline aqueous solution for use in the extraction if having a pH less than the range, may hardly help the cell walls of Corchorus capsularis L. and/or Corchorus aestuans L. to swell and may cause lower
  • the system (resulting mixture) may have a pH of typically from about 5.5 to about 13, preferably from 5.5 to 12, particularly preferably from 5.5 to 11, and most preferably from 6 to 10.
  • the raw material is preferably subjected to a pulverization treatment before the extraction treatment.
  • the extraction may be performed at a temperature of typically from about 10°C to about 90°C, preferably from 15°C to 60°C, and particularly preferably from 20°C to 40°C.
  • the extraction when performed at a temperature within the range, enables efficient extraction of a polymer compound from Corchorus capsularis L. and/or Corchorus aestuans L. and can prevent decomposition of the extracted polymer compound.
  • the extraction may be performed for a time of typically one hour or longer and preferably from 2 to 5 hours .
  • Step 2 is the step of isolating and purifying the polymer compound extracted in Step 1.
  • the polymer compound may be isolated by one or more common processes for use in purification of polymer compounds. The processes are exemplified by filtration, concentration, precipitation, crystallization, and cooling-solidification. In a preferred embodiment according to the present invention, initially, an extract is separated and recovered from a mixture of the extract and a residue of the raw material.
  • extract herein refers to a liquid containing the extracted polymer compound as being dissolved therein.
  • the separation and recovery may be performed typically by a process of subjecting the mixture to filtration; a process of
  • the extract to be subjected to Step 2 preferably has a pH of from about 6 to about 7, and more specifically from 5.5 to 7.0. This pH range is preferred because the extract does not cause corrosion typically of facilities to be used, offers better handleability, and does not cause the
  • the acid may be at least one selected from inorganic acids and organic acids.
  • the inorganic acids are exemplified by hydrochloric acid, sulfuric acid, phosphoric acid, and nitric acid.
  • the organic acids are. exemplified by acetic acid, formic acid, citric acid, oxalic acid, methanesulfonic acid, and p-toluenesulfonic acid. The end point of
  • neutralization may be determined typically with a pH meter or pH indicator paper.
  • the filtration may be performed as natural filtration, or may be performed as vacuum filtration or pressure
  • a membrane filter for use in the filtration is preferably one having a pore size of from about 10 to about 200 ⁇ .
  • the centrifugal separation may be performed typically by centrifugally separating the mixture at 1000 rpm for 10 minutes.
  • the filtration and/or centrifugal separation is preferably performed until the content of water-insoluble matter become 1 percent by weight or less (preferably 0.1 percent by weight or less).
  • separation may be performed once or repeated multiple times.
  • the extract after being separated and recovered may be subjected further to a treatment such as concentration, precipitation, crystallization, and/or cooling- solidification to give a target polymer compound as a solid.
  • a treatment such as concentration, precipitation, crystallization, and/or cooling- solidification to give a target polymer compound as a solid.
  • the extract is poured into a poor solvent to allow the polymer compound to precipitate (or to
  • the poor solvent for use in the precipitation and reprecipitation is preferably an organic solvent having a lower solubility parameter (SP) as compared with water.
  • organic solvent is exemplified by alcohols such as methanol, ethanol, propanol, 2-propanol, and butanol;
  • aliphatic hydrocarbons such as hexane, heptane, octane, and decane
  • alicyclic hydrocarbons such as cyclohexane
  • aromatic hydrocarbons such as benzene, toluene, and xylenes
  • ketones such as acetone, methyl ethyl ketone and cyclohexanone ;
  • esters such as methyl acetate, ethyl acetate, and butyl acetate; ethers such as ethyl ether, butyl ether, ethylene glycol dimethyl ether, and tetrahydrofuran; nitriles such as acetonitrile; amides such as N, N-dimethylformamide;
  • carboxylic acids such as acetic acid; halogenated
  • hydrocarbons such as methylene chloride and chloroform
  • a solvent mixture of water and an alcohol e.g., methanol
  • the solvent mixture is inexpensively available, has a low boiling point, and can thereby be purified and reused at low cost.
  • the solvent mixture of water and an alcohol preferably contains the alcohol in such a concentration that a
  • supernatant after precipitation (or reprecipitation) of the polymer compound contains the alcohol in a concentration of typically from about 40 to about 80 percent by weight, preferably from 50 to 70 percent by weight, and particularly preferably from 55 to 65 percent by weight.
  • the solvent mixture when containing the alcohol in a concentration within the range, allows the polymer compound to be highly purified with a low content of a low-molecular-weight
  • the low-molecular-weight compound is formed by decomposition of the polymer compound.
  • reprecipitatxon may be deliquored typically by filtration and dried to give a powder.
  • the drying may be performed by natural drying (air drying) , or artificial drying such as heat drying or vacuum drying.
  • the method can efficiently give a polymer compound from the raw material, where the polymer compound offers an excellent thickening effect.
  • the thickener for fossil resource extraction (or
  • thickening composition for fossil resource extraction includes the polymer compound.
  • the term "fossil resource” refers to a fossil resource that is distributed as an oil or gas and lies in a geologic formation 500 m to 4000 m underground.
  • the thickener for fossil resource extraction according to the present invention may contain the polymer compound in a content of 60 percent by weight or more, preferably 70 percent by weight or more, and particularly preferably 80 percent by weight or more, based on the total amount of the thickener.
  • the thickener for fossil resource extraction according to the present invention may include the polymer compound alone or in combination with another component such as a thickening compound other than the polymer compound. In the latter case, the thickener may contain the other component in a content of typically less than 40 percent by weight, preferably 30 percent by weight or less,
  • the thickener for fossil resource extraction according to the present invention contains the polymer compound having the above-described properties and has a viscosity equal to or higher than that of guar gum.
  • the thickener for fossil resource extraction according to the present invention contains the polymer compound having the above-described properties and has a viscosity equal to or higher than that of guar gum.
  • the thickener has excellent salt tolerance and can continuously and stably exhibit a thickening effect even in the presence of a salt. The thickener is therefore
  • a thickener for a fluid for use in extraction of fossil resources i.e., a thickener for a fluid for fossil resource extraction
  • the fluid for fossil resource extraction according to the present invention is a fluid for use in extraction
  • (mining) of fossil resources includes, as a thickener, the thickener for fossil resource extraction.
  • the fluid for fossil resource extraction may contain the thickener in a content of typically from about 0.01 to about 5 percent by weight, based on the total amount (100 percent by weight) of the fluid, where the content is adjustable as needed.
  • the fluid for fossil resource may contain the thickener in a content of typically from about 0.01 to about 5 percent by weight, based on the total amount (100 percent by weight) of the fluid, where the content is adjustable as needed.
  • extraction may contain the polymer compound in a content of typically from about 0.01 to about 5 percent by weight, based on the total amount (100 percent by weight) of the fluid, where the content is also adjustable as needed.
  • the fluid for fossil resource extraction may contain one or more of other components in addition to the thickener for fossil resource extraction.
  • Such other components are exemplified by water, a granular proppant (such as sand or silica sand), and various chemical substances.
  • the chemical substances are exemplified by acids such as hydrochloric acid; antiseptic agents (preservatives); friction reducers; and pH adjusters.
  • the fluid for fossil resource extraction may contain water and the granular proppant in a total content of typically 30 percent by weight or more (e.g., from about 30.00 to about 99.99 percent by weight),
  • preferably 50 percent by weight or more e.g., from 50.00 to 99.97 percent by weight
  • particularly preferably 80 percent by weight or more e.g., from 80.00 to 99.97 percent by weight
  • the fluid for fossil resource extraction according to the present invention contains the thickener for fossil resource extraction, can thereby maintain a suitable
  • the mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate leaves (raw material residue) from a filtrate..
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate leaves (raw material residue) from a filtrate.
  • the filtrate was added dropwise to a 75 percent by weight methanol aqueous solution in an amount four times the weight of the filtrate to give precipitates.
  • the supernatant had a methanol concentration of 60 percent by weight .
  • the precipitates were deliquored properly, washed with a 75 percent by weight methanol aqueous solution in an amount one-fourth the weight of the filtrate, deliquored, and yielded 68 g of a wet powder.
  • the wet powder was dried in a vacuum dryer at 40 °C in full vacuum overnight and yielded 12.0 g of a polymer compound (1) in a yield of 4.4 percent by weight.
  • the polymer compound (1) had a
  • solubility of 5 g per 100 g of water at a temperature of 25°C and a pH of 7.0.
  • the obtained polymer compound (1) was dissolved in water to a polymer compound concentration of 1 percent by weight, left stand at 30°C overnight, and yielded a slurry.
  • the viscosity of the slurry was measured at 25°C using a rheometer. The results are given in Fig. 1.
  • the polymer compound (1) was dissolved in water to a polymer compound concentration of 0.2 percent by weight and yielded a slurry, and the viscosity of the slurry was measured at 25°C using a rheometer. The results are given in Fig. 2.
  • the polymer compound (1) was dissolved in water respectively to concentrations of 1.5, 1.0, and 0.7 percent by weight to give slurries.
  • the slurries were each combined with NaCl to give NaCl-added slurries having a NaCl concentration of 10 percent by weight.
  • the viscosities of the slurries and the NaCl-added slurries were measured using a rheometer to evaluate the salt tolerance. The results are given in Table 1.
  • the salt tolerance evaluation demonstrates that the polymer compound according to the present invention had not a decreased viscosity but rather an increased viscosity even in the presence of NaCl. This demonstrates that the polymer compound according to the present invention has excellent salt tolerance.
  • a mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • the filtrate was added dropwise to 100 percent by weight methanol in an amount four times the weight of the filtrate to give precipitates.
  • the supernatant had a methanol concentration of 80 percent by weight.
  • the precipitates were deliquored properly, washed with a 75 percent by weight methanol aqueous solution in an amount one-fourth the weight of the filtrate, deliquored, and yielded 160 g of a wet powder.
  • the wet powder was dried in a vacuum dryer at 40 °C in full vacuum overnight and yielded 16.9 g of a polymer compound (2) in a yield of 5.1 percent by weight.
  • the polymer compound (2) had a
  • solubility of 5 g per 100 g of water at a temperature of 25°C and a pH of 7.0.
  • Corchorus capsularis L. were placed. The leaves were then combined with 180 g of a 0.1 N NaOH agueous solution (pH 13), followed by an extraction treatment with stirring at 50°C for 2 hours. The mixture at the completion of extraction had a pH of 9.4.
  • the 0.1 N NaOH aqueous solution had been prepared by 50-fold dilution of a 5 N NaOH aqueous solution (supplied by Wako Pure Chemical Industries, Ltd.).
  • the resulting mixture was subjected to a neutralization treatment with 4 g of 3.5 percent by weight hydrochloric acid. The completion of neutralization was determined using a pH indicator paper.
  • the mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • the filtrate was added dropwise to 100 percent by weight methanol in an amount four times the weight of the filtrate to give precipitates.
  • the supernatant had a methanol concentration of 80 percent by weight.
  • the precipitates were deliquored properly, washed with a 75 percent by weight methanol aqueous solution in an amount one-fourth the weight of the filtrate, and deliquored to give a wet powder.
  • the wet powder was dried in a vacuum dryer at 40 °C in full vacuum overnight and yielded 0.17 g of a polymer compound (3) in a yield of 4.0 percent by weight.
  • the polymer compound (3) had a solubility of 6 g per 100 g of water at a temperature of 25 °C and a pH of 7.0.
  • a polymer compound (4) was prepared by the procedure of Example 1, except for using an alkaline aqueous solution having a pH of 12.5 in the extraction step.
  • the polymer compound (4) was obtained in a yield of 2.0 percent by weight and had a solubility of 4 g per 100 g of water at a temperature of 25 °C and a pH of 7.0.
  • the mixture upon the completion of extraction had a pH of 8.4.
  • a polymer compound (5) was prepared by the procedure of Example 1, except for using an alkaline aqueous solution having a pH of 12 in the extraction step.
  • the polymer compound (5) was prepared in a yield of 1.9 percent by weight and had a solubility of 4 g per 100 g of water at a temperature of 25 °C and a pH of 7.0.
  • the mixture upon the completion of extraction had a pH of 6.4.
  • a polymer compound (6) was prepared by the procedure of Example 1, except for using an alkaline aqueous solution having a pH of 11 in the extraction step.
  • the polymer compound (6) was prepared in a yield of 1.7 percent by weight and had a solubility of 4 g per 100 g of water at a temperature of 25 °C and a pH of 7.0.
  • the mixture upon the completion of extraction had a pH of 5.8.
  • the mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • the filtrate was added dropwise to 100 percent by weight methanol in an amount four times the weight of the filtrate to give precipitates.
  • the supernatant had a methanol concentration of 80 percent by weight.
  • the precipitates were deliquored properly, washed with a 75 percent by weight methanol aqueous solution in an amount one-fourth the weight of the filtrate, and deliquored to give a wet powder.
  • the wet powder was dried in a vacuum dryer at 40 °C in full vacuum overnight and yielded 0.67 g of a polymer compound (7) in a yield of 6.7 percent by weight.
  • the obtained polymer compound (7) was treated to give a slurry having a concentration of 1 percent by weight, and the viscosity of the slurry was measured. The results are given in Fig. 1.
  • Corchorus capsularis L. were placed. The leaves were then combined with 180 g of a 0.5 N NaOH aqueous solution (pH 13.5) and subjected to an extraction treatment with stirring at 50 °C for 2 hours. The mixture at the completion of extraction had a pH of 12.9.
  • the 0.5 N NaOH aqueous solution pH 13.5
  • the mixture was then subjected to a neutralization treatment with 85 g of 3.5 percent by weight hydrochloric acid. The completion of neutralization was determined using a pH indicator paper.
  • the mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC eshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC eshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • the filtrate was added dropwise to 100 percent by weight methanol in an amount four times the weight of the filtrate to give precipitates.
  • the supernatant had a methanol concentration of 80 percent by weight.
  • the precipitates were deliquored properly, washed with a 75 percent by weight methanol aqueous solution in an amount one-fourth the weight of the filtrate, and deliquored to give a wet powder.
  • the wet powder was dried in a vacuum dryer at 40 °C in full vacuum overnight and yielded 0.53 g of a polymer compound (8) in a yield of 5.3 percent by weight.
  • the obtained polymer compound (8) was treated to give a slurry having a concentration of 1 percent by weight, and the viscosity of the slurry was measured. The results are given in Fig. 1.
  • the leaves were then separated from a filtrate, placed in a reactor, combined with 50 mL of diethyl ether (supplied by Wako Pure Chemical Industries, Ltd.) and 50 mL of ethanol (supplied by Wako Pure Chemical Industries, Ltd.), followed by delipidation with stirring at 50°C for 30 minutes.
  • the leaves were separated from a filtrate, placed again in the reactor, and combined with 50 mL of diethyl ether (supplied by Wako Pure Chemical Industries, Ltd.) and 50 mL of
  • the mixture obtained through the neutralization step was subjected to vacuum filtration using a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • a vacuum pump with a nonwoven fabric (trade name T-ND 200T, supplied by NBC Meshtec Inc.) as a filter cloth to separate a filtrate from residual leaves.
  • the filtrate was added dropwise to 100 percent by weight ethanol in an amount two times the weight of the filtrate to give precipitates.
  • the precipitates were deliquored properly, washed with two portions of 70 g of a 75 percent by weight ethanol aqueous solution, and deliquored to give a wet powder.
  • the wet powder was freeze-dried and yielded 0.7 g of a polymer compound (9) in a yield of 3.9 percent by weight.
  • the obtained polymer compound (9) was treated to give a slurry having a concentration of 1 percent by weight, and the viscosity of the slurry was measured. The results are given in Fig. 1.
  • Guar gum derived from guar cluster bean ⁇ Cyamopsis tetragonoloba) as a Leguminous plant was prepared as a product under the trade name of IGGUAR FG-88L (supplied by INDIA GLYCOLS LIMITED) .
  • the guar gum was treated to give a slurry having a guar gum concentration of 0.2 percent by weight, and the .viscosity of the slurry was measured using a rheometer. The 'results are given in Fig. 2.
  • Measuring device rheometer (trade name MCR-301, supplied by Anton Paar GmbH)
  • Example 2 An aliquot (3 mg) of the polymer compound (1) obtained in Example 1 was combined with 1 g of deuterium oxide (D 2 0) as a solvent and left stand overnight. A sample (0.7 mL) was sampled from the resulting aqueous solution, placed in a sample tube, and subjected to ⁇ H-NMR measurement.
  • D 2 0 deuterium oxide
  • HORIBA FT-720 Spectrophotometer supplied by HORIBA, Ltd.
  • the polymer compounds can be simply produced from a raw material that is easily available.
  • the polymer compounds have excellent salt tolerance and can continuously and stably exhibit a thickening effect even in the presence of a salt.
  • the polymer compounds are highly biodegradable and load a small burden on the environment.
  • engineering materials e.g., adhesive coating agents and concrete admixtures

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • General Health & Medical Sciences (AREA)
  • Sustainable Development (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Lubricants (AREA)
  • Processing Of Solid Wastes (AREA)

Abstract

L'invention concerne un composé polymère qui est disponible à partir d'une plante comme matière première, qui peut être facilement extrait depuis la matière première, qui ne présente absolument pas de risque, pèse peu sur l'environnement, et fait preuve d'un excellent effet épaississant, où la plante a été éliminée de manière classique comme déchet. Le composé polymère est extrait depuis Corchorus capsularis L. et/ou de Corchorus aestuans L. et présente une viscosité au cisaillement de 0,2 Pa.s ou plus à une température de 25 ℃ et une vitesse de cisaillement de 10 (1/s) en solution aqueuse contenant 1 pour cent en poids du composé polymère.
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JP2011006581A (ja) * 2009-06-25 2011-01-13 Kohjin Co Ltd 感温性を有する水溶性増粘剤
WO2015064388A1 (fr) * 2013-11-01 2015-05-07 株式会社ダイセル Procédé de production d'un composé polymère

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CN110432478A (zh) * 2019-08-12 2019-11-12 中国农业科学院麻类研究所 一种饮料增稠剂的制备方法及其产品与应用

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