WO2015199481A1 - 구형 푸란 수지 입자 제조방법 - Google Patents

구형 푸란 수지 입자 제조방법 Download PDF

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Publication number
WO2015199481A1
WO2015199481A1 PCT/KR2015/006534 KR2015006534W WO2015199481A1 WO 2015199481 A1 WO2015199481 A1 WO 2015199481A1 KR 2015006534 W KR2015006534 W KR 2015006534W WO 2015199481 A1 WO2015199481 A1 WO 2015199481A1
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WIPO (PCT)
Prior art keywords
weight
furan resin
parts
furfuryl alcohol
spherical
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PCT/KR2015/006534
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English (en)
French (fr)
Korean (ko)
Inventor
강세연
성은진
송세현
손세일
이홍우
박찬수
남우근
이진구
Original Assignee
대원제약주식회사
주식회사 퓨어스피어
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Priority to JP2016576078A priority Critical patent/JP6557687B2/ja
Priority to CN201580035063.3A priority patent/CN106661173B/zh
Publication of WO2015199481A1 publication Critical patent/WO2015199481A1/ko

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
    • B01J20/20—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising free carbon; comprising carbon obtained by carbonising processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
    • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C08G65/36—Furfuryl alcohol
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating

Definitions

  • the present invention relates to a method for producing spherical furan resin particles, and to a method for producing spherical furan resin particles by three-way mixing using furfuryl alcohol, aldehydes, and urea, and a spherical furan resin obtained thereby.
  • Furan resin refers to phenol furfural resin, furfural acetone resin, furfuryl alcohol resin and the like obtained from furfural or furfuryl alcohol.
  • Furfural is a very useful general purpose chemical which is widely used in recent years as a fine chemical intermediate material, a solvent, and a resin raw material for a special use.
  • furan aldehydes greener purol-furfural of the formula is a C 5 H 4 O 2 as a furan-2-hydroxy to Cavalli (furan-2-carbaldehyde) or an aromatic aldehyde is an aldehyde group CHO attached to the furan ring of the ring structure.
  • Furan resin is a thermosetting plastic containing furangori, it is a liquid in appearance, but is cured by heat and used as a water-resistant adhesive.
  • flexible furan resin can be obtained, and it has excellent durability against oil, acid, alkali, and solvent.
  • adhesive coating is applied with epoxy resin, both defects are compensated for each other, and the corrosion resistance, It is possible to obtain a material having properties excellent in heat resistance, adhesion of epoxy resins and deformation.
  • furan resins use acid catalysts, which are heated at relatively low temperatures to form intermediates and finally heat cured at high temperatures. Since it has excellent alkali resistance, it is used for linings applied to the inside of reaction vessels or storage tanks using acid alkali by reinforcing glass fibers as resin cement.
  • the low viscosity furan resin the initial condensate of furfuryl alcohol, is soluble in alcohol, the higher viscosity is partially soluble in alcohol, soluble in ethyl acetate, acetone, aromatic hydrocarbons, furfural, furfuryl alcohol, If it is made neutral, it is stable even if it is preserved for a long time.
  • thermosetting furan resin excellent in chemical resistance is produced.
  • Conventional Japanese Patent Application Laid-Open No. 2011-157463 uses furfuryl alcohol alone, and spherical furfuryl alcohol by self-condensation reaction using an acid catalyst such as alkylbenzenesulfonic acid having a pKa of less than 1,5 in the presence of a protective colloid.
  • an acid catalyst such as alkylbenzenesulfonic acid having a pKa of less than 1,5 in the presence of a protective colloid.
  • Disclosed is a method for producing resin particles, and the use of aldehydes is excluded, but there is a problem in that the pKa of the acid catalyst to be used must be limited.
  • Japanese Laid-Open Patent Publication No. 2011-157464 discloses a method for producing spherical furan-aldehyde resin particles using an acid catalyst such as alkylbenzenesulfonic acid in furfuryl alcohol and aldehydes in the presence of protective colloids.
  • Korean Patent Publication No. 2013-035781 discloses spherical activated carbon particles formed by carbonizing spherical furan resin particles obtained by reacting furfuryl alcohol and aldehydes in the presence of a catalyst and a protective colloid. There is a disadvantage in that excessive use of aldehydes harmful to the human body, such as to stimulate.
  • furfuryl alcohol alone or mixed to emphasize the use of organic acids having a large molecular weight, such as inorganic acid or alkylbenzene sulfonic acid containing a benzene ring when preparing the resin, it is mainly liquid, so care must be taken when storing and using .
  • the present inventors have completed the present invention by developing a safer furan resin manufacturing method while studying to solve the technical and safety problems shown in the furan resin manufacturing method from the conventional furfuryl alcohol.
  • the present invention has been made to solve the problems of the prior art, the object of the present invention is not only to significantly reduce the amount of toxic aldehydes, but also to limit the pKa of the acid catalyst, a benzene ring that has a harmful effect on the human body It is to provide a spherical furan resin particle method that can improve the workability and further obtain a high strength by using a low molecular weight acid catalyst having a simple structure that is easy to handle because it does not contain.
  • the present invention (a) mixing step of mixing a mixed solution of urea, furfuryl alcohol, water in the reactor; (b) adjusting the pH of the mixed solution to pH 7.5 to pH 9.5; (c) a step of introducing aldehydes, acid catalyst and gum into the reactor; (d) A furan resin particle manufacturing method comprising a curing step of curing the furan resin.
  • aldehydes are based on molar ratio 1 based on furfuryl alcohol, 0.01 to 0.25 mol, urea based on molar ratio 1 based on furfuryl alcohol, 0.02 to 0.26 moles, and water is 0.5 based on 100 parts by weight of furfuryl alcohol. It may be mixed by weight times ⁇ 15 weight times.
  • the acid catalyst may have 3 to 4 carbon atoms that do not include a benzene ring, and the acid catalyst is 0.1 parts by weight to 10 parts by weight based on 100 parts by weight of furfuryl alcohol.
  • Spherical furan resin particle can be obtained by said manufacturing method.
  • the spherical activated carbon particles can be obtained through the carbonization and steam activation process for the produced spherical furan resin particles.
  • the use of aldehydes can be significantly reduced by mixing a small amount of urea at the time of producing spherical furan resin particles, and it is possible to use acid catalyst without using conventional inorganic acid or alkylbenzene sulfonic acid type.
  • the compressive strength of the furan resin particles produced therefrom and the spherical activated carbon obtained therefrom is also not limited to the pKa value of.
  • Example 1 is a photograph taken by enlarging the spherical furan resin synthesized in Example 1 at 100 magnification
  • Example 2 is a photograph taken by enlarging the spherical furan resin synthesized in Example 2 at 100 magnification
  • Example 3 is a photograph taken by enlarging the spherical furan resin synthesized in Example 3 at 100 magnification
  • the present invention significantly reduces the use of toxic aldehydes by selecting furfuryl alcohol as a conventional phenol substitute and by adding urea, and a benzene ring such as alkylbenzenesulfonic acid rather than strong acids such as sulfuric acid and hydrochloric acid. It relates to a method for easily preparing furan resin particles using organic acids having a simple structure (for example, maleic acid and malonic acid) rather than the acid type.
  • Aldehydes used in the present invention means a compound containing an aldehyde group or a substance used to prepare such a compound or prepared by reacting with such a compound.
  • formaldehyde is suitably used.
  • the formaldehyde supply materials such as formalin, paraformaldehyde, trioxane, tetraoxane, acetal can be suitably used in consideration of reactivity, raw material price and the like.
  • the urea used in the present invention is in a solid grain state and is added to the reaction without the need for melting or pulverizing it specifically for the reaction, so that the workability is good and the cost is advantageous.
  • the compounding ratio of aldehydes and urea may be 0.01 to 0.25 mol (1 to 22 parts by weight of 35% by weight aqueous formaldehyde solution based on 100 parts by weight of furfuryl alcohol), preferably aldehydes per mole of furfuryl alcohol. Is 0.07 mol to 0.18 mol (6-16 parts by weight of 35% by weight aqueous formaldehyde solution based on 100 parts by weight of furfuryl alcohol).
  • Urea is 0.01 to 0.26 mol (0.6 to 16 parts by weight based on 100 parts by weight of furfuryl alcohol), preferably 0.08 to 0.19 moles (based on 100 parts by weight of furfuryl alcohol) per mole of furfuryl alcohol on a molar basis. 5 to 11.6 parts by weight). If the amount of aldehydes and urea used per mole of furfuryl alcohol increases, particle generation does not proceed, desired particles are not obtained, or the reaction proceeds slowly.
  • the amount of water used in the present invention may be a ratio of about 0.5 to 15 times by weight based on 100 parts by weight of furfuryl alcohol. If the amount of water is less than 0.5 wt. Times, the reactant may be lumped into an ovoid shape. If the amount of water is used more than 15 wt. Times, the reaction time becomes long, which causes difficulty in manufacturing.
  • Dispersion stabilizer in the present invention acts on the surface in the dispersion process of the particles, it is used to delay the aggregation, and can be used to select one or two or more kinds of water-soluble polymers such as gum, methyl cellulose, hydroxy ethyl cellulose. Arabian gum can be used as appropriate.
  • the acid catalyst used in the present invention is generally used in an amount of 0.1 to 10 parts by weight, preferably 0.5 to 4 parts by weight, based on 100 parts by weight of furfuryl alcohol.
  • the acid catalyst mentioned in the present invention is in a solid state, and does not need to be dissolved in water to make a solution state, but may be mixed in the process of stirring during preparation.
  • the reaction time may be long or hardening of the produced particles may be difficult, and when the amount of the acid catalyst is used, it may be difficult to produce agglomerates or to obtain desired microparticles.
  • the base used in the present invention is to make the atmosphere of the initial reactant to a basic atmosphere, and bases such as sodium hydroxide, potassium hydroxide, barium hydroxide may be used, and sodium hydroxide may be suitably used.
  • the basic atmosphere used in the present invention is pH 7.5 to 9.5, preferably pH 8-9 is suitably used. If the pH is not basic, the initial reaction does not proceed, and if the pH is too high, side reactions may occur in which aldehydes are not beneficial to the reaction.
  • reaction temperature of this invention is 50 degreeC or more temperature, Preferably it is 70 degreeC or more.
  • the reaction time is appropriately applied considering the reaction temperature, the state of the intermediate product, the state of particle curing, etc., but generally, about 2 to 30 hours are applied.
  • Spherical furan resin particles are obtained by filtering and washing the reactants produced by the above method, followed by drying.
  • Porous activated carbon with increased strength means that the spherical furan resin is carbonized and steam activated (heated at a temperature of 500 ° C. for 1 hour, carbonized, and heated to 900 ° C. under steam at 140 ° C. using a rotary external heat furnace for 140 minutes).
  • steam activated heat activated
  • the strength of the porous activated carbon has a strength of at least 2 times up to 10 times higher than that of the activated carbon prepared by using pitch as a raw material.
  • the compressive strength is significantly low, and therefore, when formulated into a solid unit dosage form as a medicine, for example, when filled into a capsule, the activated carbon may be broken during the filling process. There was a losing problem.
  • the oral adsorbent since the oral adsorbent is close to several g at a single dose, it is often caused by discomfort such as vomiting when taking it as a powder. Therefore, in practice, the oral adsorbent uses an auxiliary means such as Orlite. Administration is made.
  • the present invention is to prepare a spherical furan resin having a high compressive strength because of the need for a unit solid preparation that can greatly improve the convenience of dosing, and to obtain a porous spherical activated carbon as a result after carbonization and steam activation.
  • the average particle diameter and compressive strength of the spherical activated carbon according to the present invention are measured by the following method.
  • a particle diffraction diagram based on volume was prepared using a laser diffraction particle size distribution device (HELOS Particle Size Analysis, manufactured by Sympatec), and the particle size corresponding to Volume Mean Diameter (VMD) was used as the average particle size.
  • HELOS Particle Size Analysis manufactured by Sympatec
  • VMD Volume Mean Diameter
  • the strength of the spherical activated carbon was measured as follows using a compressive strength analyzer (AFK-500TE manufactured by Digitech).
  • One spherical activated carbon sample to be measured was placed in the middle of the compressive strength tip, and then the compressive strength was lowered at a speed of 20 mm / min to determine the compressive strength value. After measuring 22 spherical activated carbon samples in the same manner as described above, the compressive strength value was determined by taking the average of 20 tablets except the maximum and minimum values.
  • the reaction product After completion of the reaction, the reaction product is cooled to room temperature, filtered and washed to obtain spherical furan resin particles.
  • the obtained spherical furan resin was measured at 100 magnification using i-Solution (manufactured by IMT i-Solution Inc.) which is an image analysis program, and is shown in FIG. 1.
  • the reaction product After completion of the reaction, the reaction product is cooled to room temperature, filtered and washed to obtain spherical furan resin particles.
  • the obtained spherical furan resin was measured at 100 magnification using i-Solution (manufactured by IMT i-Solution Inc.) which is an image analysis program, and is shown in FIG. 2.
  • the reaction product After completion of the reaction, the reaction product is cooled to room temperature, filtered and washed to obtain spherical furan resin particles.
  • the obtained spherical furan resin was measured at 100 magnification using i-Solution (manufactured by IMT i-Solution Inc.) which is an image analysis program, and is shown in FIG. 3.
  • the reaction product After completion of the reaction, the reaction product is cooled to room temperature, filtered and washed to obtain furan resin.
  • the obtained spherical furan resin was measured at 40 magnification using i-Solution (manufactured by IMT i-Solution Inc.) which is an image analysis program, and is shown in FIG. 4.
  • the spherical furan resin particles obtained in Examples 1, 2, and 3 were carbonized by heating at 500 ° C. for 1 hour in a nitrogen atmosphere using an external thermal rotary kiln, and the spherical carbon particles obtained here were subjected to nitrogen using an external thermal rotary kiln.
  • Spherical activated carbon was obtained by injecting steam in the atmosphere and heating it at 900 degrees for 140 minutes, which is called an activation process. Average particle diameter and compressive strength results for each of the examples are shown in the table below.
  • a small amount of urea can be used by mixing a small amount of urea, and it has a high compressive strength even if the acid catalyst has a high pKa without using an inorganic acid or an alkylbenzenesulfonic acid type.
  • Spherical furan resin particles were obtained.
  • the compressive strength of the spherical activated carbon obtained from the spherical furan resin particle manufactured by this invention is also high, and it is easy to handle.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Phenolic Resins Or Amino Resins (AREA)
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PCT/KR2015/006534 2014-06-27 2015-06-26 구형 푸란 수지 입자 제조방법 WO2015199481A1 (ko)

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JP2016576078A JP6557687B2 (ja) 2014-06-27 2015-06-26 球形フラン樹脂粒子の製造方法
CN201580035063.3A CN106661173B (zh) 2014-06-27 2015-06-26 球形呋喃树脂粒子的制备方法

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KR1020140079750A KR101592882B1 (ko) 2014-06-27 2014-06-27 구형 푸란 수지 입자 제조방법

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WO2016168675A1 (en) * 2015-04-15 2016-10-20 Micromidas, Inc. Activated carbon materials, and methods of preparing thereof and uses thereof
US10221275B2 (en) * 2014-08-29 2019-03-05 Sekisui Chemical Co., Ltd. Furan resin, method for producing same, thermosetting furan resin composition, cured product, and furan resin composite

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KR102133882B1 (ko) * 2018-11-19 2020-07-14 (주)코멕스카본 구형 페놀수지 및 이의 제조방법
KR20240094809A (ko) * 2022-12-16 2024-06-25 코오롱인더스트리 주식회사 비드 및 이를 이용하여 제조된 폴리에틸렌 중합체

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