WO2020251227A1 - Nouveau composé de réticulation et polymère préparé à l'aide de celui-ci - Google Patents

Nouveau composé de réticulation et polymère préparé à l'aide de celui-ci Download PDF

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Publication number
WO2020251227A1
WO2020251227A1 PCT/KR2020/007393 KR2020007393W WO2020251227A1 WO 2020251227 A1 WO2020251227 A1 WO 2020251227A1 KR 2020007393 W KR2020007393 W KR 2020007393W WO 2020251227 A1 WO2020251227 A1 WO 2020251227A1
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WIPO (PCT)
Prior art keywords
crosslinking agent
formula
polymer
agent compound
acrylate
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PCT/KR2020/007393
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English (en)
Korean (ko)
Inventor
임원택
김용진
김기철
김기현
Wonmun CHOI (최원문)
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020200065291A external-priority patent/KR102495827B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2021530769A priority Critical patent/JP7139016B2/ja
Priority to US17/271,802 priority patent/US20210324174A1/en
Priority to EP20822857.7A priority patent/EP3819334B1/fr
Priority to CN202080004400.3A priority patent/CN112533891B/zh
Publication of WO2020251227A1 publication Critical patent/WO2020251227A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F120/04—Acids; Metal salts or ammonium salts thereof
    • C08F120/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids

Definitions

  • the present invention relates to a novel crosslinking agent compound and a polymer prepared using the same. More specifically, it relates to a novel crosslinking agent compound in which the generation of volatile substances and decomposition products is prevented in advance because thermal decomposition does not occur at one end, and a polymer prepared using the same.
  • Super Absorbent Polymer is a synthetic polymer material that can absorb moisture of 500 to 1,000 times its own weight, and each developer has a Super Absorbency Material (SAM), AGM (Absorbent Gel). Material) and so on. Since the above superabsorbent resins have begun to be put into practical use as sanitary tools, nowadays, in addition to hygiene products such as paper diapers and sanitary napkins for children, soil repair agents for horticulture, civil engineering and construction materials, sheets for seedlings, freshness maintenance agents in the food distribution field. , And is widely used as a material for poultice.
  • SAM Super Absorbency Material
  • AGM Absorbent Gel
  • the base resin in order for the superabsorbent polymer to have excellent performance, the most important polymer, the base resin, must have a high absorbency.
  • the crosslinking density inside the polymer can be controlled.
  • the internal crosslinking agent is for crosslinking the interior of the polymer in which the acrylic acid-based monomer is polymerized, that is, the base resin, and the internal crosslinking density of the base resin can be adjusted according to the type and content of the internal crosslinking agent. If the crosslinking density of the base resin is low, the water absorption capacity is high, but the strength is weak, so there may be a problem that the shape cannot be maintained in the subsequent process.If the crosslinking density is too high, the strength is increased but the water absorption ability may be lowered. And it is very important to control the appropriate crosslinking density from the viewpoint of absorption capacity.
  • super absorbent polymers prepared by polymerizing acrylic acid monomers have a characteristic odor of acrylic acid, and when used in hygiene products such as diapers, unpleasant odors are also accompanied when excreting body fluids such as urine, which effectively reduces such odors. Required.
  • a method of mixing and using a porous adsorption material with a super absorbent polymer has been developed.
  • Japanese Patent Laid-Open No. 2008-522003 discloses a crosslinking agent compound used in the manufacture of a super absorbent polymer.
  • the compound contains acrylate at both ends and is used as a crosslinking agent, the acrylate ends may be decomposed, and at this time, volatile substances such as 2-Methyl-1,3-Butadiene (VOC; Volatile Organic Compounds) and decomposition
  • VOC Volatile Organic Compounds
  • Patent Document 1 Japanese Patent Publication No. 2008-522003
  • An object of the present invention is to provide a novel crosslinking agent compound in which the generation of volatile substances (VOC) and decomposition products is reduced because thermal decomposition does not occur at one end, and a polymer prepared using the same.
  • VOC volatile substances
  • the present invention provides a crosslinking agent compound represented by the following Formula 1:
  • R 1 and R 2 are each independently hydrogen or methyl
  • R 3 , R 4 , R 5 and R 6 are each independently hydrogen, C 1-20 alkyl, or C 3-20 cycloalkyl,
  • X is O, S, or CH 2 ,
  • n is an integer of 2 to 10.
  • the present invention provides a polymer in which the crosslinking agent compound and an acrylic acid-based monomer are polymerized.
  • alkyl refers to a linear or branched saturated monovalent hydrocarbon of 1 to 20, preferably 1 to 10, more preferably 1 to 5 carbon atoms.
  • alkyl include methyl, ethyl, propyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, n-pentyl, isopentyl , Neopentyl, tert-pentyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1 -Methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-
  • cycloalkyl refers to 3 to 20, preferably 3 to 10, more preferably 5 to 10 saturated aliphatic cyclic monovalent hydrocarbons.
  • examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like, but the present invention is not limited thereto.
  • crosslinking agent compound according to an embodiment of the present invention is represented by Chemical Formula 1.
  • R 1 and R 2 may be hydrogen.
  • the R 3 , R 4 , R 5 and R 6 may each independently be hydrogen, C 1-10 alkyl, or C 3-10 cycloalkyl,
  • R 3 , R 4 , R 5 and R 6 may each independently be hydrogen or C 1-10 alkyl
  • R 3 , R 4 , R 5 and R 6 may each independently be hydrogen or methyl.
  • R 3 and R 4 may be methyl.
  • each of R 5 and R 6 is independently hydrogen or methyl, and at least one of R 5 and R 6 may be hydrogen.
  • R 3 and R 4 are methyl
  • R 5 and R 6 are each independently hydrogen or methyl
  • at least one of R 5 and R 6 may be hydrogen.
  • X may be O, or CH 2 .
  • n may be an integer of 2 to 5.
  • n may be 2 or 3
  • n may be 2.
  • the compound represented by Formula 1 may be represented by any one of Formulas 1-1 to 1-4, but the present invention is not limited thereto:
  • the use of the compound represented by Formula 1 is not limited thereto, but may be used as a crosslinking agent during polymerization with an acrylic acid-based monomer in the manufacturing process of the super absorbent polymer.
  • One end of the crosslinking agent compound represented by Formula 1 contains an acrylate that is decomposed by heat, while the other end contains alkenyl that is not decomposed by heat. Therefore, when heated, the acrylate end is thermally decomposed, but the crosslinking agent compound does not decompose at the alkenyl end, so the amount of volatile organic compounds (VOC, Volatile Organic Compounds) and decomposition products that cause odors decreases, and as a result, superabsorbent resins, etc. If used as a odor can be prevented.
  • VOC volatile organic compounds
  • the crosslinking agent compound of Formula 1 may be prepared according to a known organic synthesis method, for example, may be prepared by the same method as in Scheme 1 below, but the present invention is not limited thereto.
  • a crosslinking agent compound represented by Formula 1 and an acrylic acid-based monomer are crosslinked and polymerized.
  • the acrylic acid-based monomer is a compound represented by the following formula (2):
  • R is an alkyl group having 2 to 5 carbon atoms containing an unsaturated bond
  • M is a hydrogen atom, a monovalent or divalent metal, an ammonium group, or an organic amine salt.
  • the acrylic acid-based monomer may include at least one selected from the group consisting of acrylic acid, methacrylic acid, and monovalent metal salts, divalent metal salts, ammonium salts, and organic amine salts thereof.
  • the acrylic acid-based monomer may have an acidic group, and at least a part of the acidic group may be neutralized.
  • polymer or “crosslinked polymer” means that the acrylic acid-based monomer is polymerized in the presence of the crosslinking agent compound of Formula 1, and may encompass all ranges of moisture content or particle size.
  • a polymer in a state before drying after polymerization and having a moisture content (moisture content) of about 40% by weight or more may be referred to as a hydrogel polymer.
  • base resin or “base resin powder” is a polymer made in the form of a powder by drying and pulverizing the polymer, and a crosslinked structure is not formed on the surface of the polymer. Means polymer.
  • the crosslinking agent compound represented by Formula 1 is a thermally decomposable internal crosslinking agent in which one end is an acrylate, and the internal crosslinking structure of the polymer obtained by crosslinking polymerization of the compound of Formula 1 and an acrylic acid-based monomer is obtained by heat (e.g., 180°C or higher). In) can be disassembled. Accordingly, crosslinking polymerization of the acrylic acid-based monomer in the presence of the crosslinking agent compound of Formula 1 can provide a crosslinked polymer into which a thermally decomposable internal crosslinked structure is introduced.
  • crosslinked polymer is introduced into a high-temperature subsequent step such as a surface crosslinking step, at least a part of the crosslinked structure derived from the compound of Formula 1 in the crosslinked polymer is decomposed. Accordingly, the internal crosslink density in the crosslinked polymer decreases.
  • the crosslinked polymer surface is further crosslinked by the surface crosslinking agent, thereby increasing the external crosslinking density.
  • the superabsorbent polymer prepared in this way may have a reduced internal crosslinking density than the base resin of the existing superabsorbent polymer. Accordingly, the super absorbent polymer may exhibit relatively improved water holding capacity compared to the existing super absorbent polymer.
  • the superabsorbent polymer may have a surface crosslinking layer that is thicker than that of the existing superabsorbent polymer by decomposing or decomposing the internal crosslinking bond. Accordingly, the super absorbent polymer may exhibit excellent absorption under pressure. Therefore, as the crosslinking density increases from the inside to the outside, the super absorbent polymer of one embodiment has various physical properties such as water holding capacity and pressure absorption capacity, unlike the conventional common knowledge that water holding capacity and pressure absorption capacity are in inverse proportion to each other. It is improved so that all of them can exhibit excellent properties.
  • the crosslinking agent compound represented by Formula 1 is an internal crosslinking agent for reducing the generation of volatile substances (VOCs) and decomposition products, and contains alkenyl that does not decompose even when heated at one end of the crosslinking agent compound. Include.
  • the conventional crosslinking agent compound has a diacrylate structure, and the acrylate is provided in an internal crosslinking structure and serves to be decomposed by heat in the manufacturing process of the super absorbent polymer. At this time, acrylate remaining before/after decomposition reacts with water to hydration, and is removed from the super absorbent polymer and vaporized to generate volatile organic compounds (VOC) and decomposition products, which may cause odors.
  • VOC volatile organic compounds
  • the crosslinking agent compound represented by Chemical Formula 1 of the present invention includes an alkenyl structure that is not thermally decomposed at one end, unlike the conventional crosslinking agent compound, thereby reducing the causes of the dropout and vaporization.
  • the polymer obtained by crosslinking polymerization of the crosslinking agent compound represented by Formula 1 and an acrylic acid monomer is a major volatile substance (VOC; Volatile Organic Compounds) and an amount of decomposition products, such as MeOH, Total sum of C4, 2-Methyl-1,3-butadiene, 2-Methyl-3-buten-2-ol, 3-Methyl-3-Buten-1-ol, etc. is 50 ppm or less, 30 ppm or less, 20 ppm or less, or 10 ppm or less.
  • C4 collectively refers to hydrocarbon compounds having various structures having 4 to 10 carbon atoms.
  • the amount of generation of the main volatile substances and decomposition products is that 0.5 g of super absorbent polymer is added to 500 ml of 0.9 wt% NaCl aqueous solution and only 2 ml of them are heated at 80° C. for 1 hour. -Measure by analyzing with GC/MS.
  • the polymer in addition to the crosslinking agent compound of Formula 1, the polymer may be crosslinked with a conventionally known internal crosslinking agent.
  • a compound containing two or more crosslinkable functional groups in a molecule may be used.
  • the conventional internal crosslinking agent include N,N'-methylenebisacrylamide, trimethylolpropane tri(meth)acrylate, ethylene glycol di(meth)acrylate, polyethylene glycol (meth)acrylate, propylene glycol di (Meth)acrylate, polypropylene glycol (meth)acrylate, butanedioldi(meth)acrylate, butylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, hexanedioldi( Meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, dipentaerythritol pentaacrylate, glycerin tri(meth)acrylate, One or more selected from the group consisting of pent
  • the polymer of the present invention is a volatile substance (VOC; Volatile Organic Compounds) and decomposition in the process of preparing a super absorbent polymer despite the thermally decomposable internal crosslinking structure due to the structural characteristics of the novel crosslinking agent compound of Formula 1 above.
  • VOC Volatile Organic Compounds
  • the amount of product generated is reduced, and the occurrence of odor is prevented while having various physical properties such as water holding capacity and pressure absorption capacity equivalent to that of a super absorbent polymer using a crosslinking agent having an acrylate at both ends. Accordingly, it exhibits a deodorizing performance that reduces the odor peculiar to a super absorbent polymer and/or odor generated when used as a hygiene product, and can provide an excellent feeling of use.
  • the superabsorbent polymer can provide hygiene products such as diapers that exhibit excellent absorption properties even through a high-temperature production process.
  • the crosslinking agent compound of the present invention is a compound of a novel structure that is not known in the art, and contains alkenyl at one end and does not cause thermal decomposition at the end, so that volatile substances (VOC; Volatile Organic Compounds) and decomposition products Odor generation can be prevented because generation is reduced.
  • VOC Volatile Organic Compounds
  • the polymer in which the crosslinking agent compound of the present invention is polymerized with an acrylic acid monomer has the same level of water holding capacity and pressure absorption capacity as those of the conventional thermally decomposable crosslinking agent, and volatile substances (VOC; Volatile Organic Compounds) generated during use. And by reducing the amount of decomposition products generated, odors may be prevented.
  • VOC Volatile Organic Compounds
  • THF was removed through distillation under reduced pressure, and the EA layer obtained by repeating extraction with EA 3 times was washed with water. Residual moisture was removed using MgSO 4 , distilled under reduced pressure, and concentrated to obtain 4-(allyloxy)-2-methylbutan-2-ol (yield 88%).
  • the upper hexane layer was separated and the lower organic salt layer was extracted once more using hexane, and the hexane layer was collected and washed with water.
  • the residual moisture in the hexane layer was removed using MgSO 4 and distilled under reduced pressure to obtain 2,6-dimethyloct-7-en-2-yl acrylate (79% yield).
  • THF was removed through distillation under reduced pressure, and the EA layer obtained by repeating extraction with EA 3 times was washed with water. Residual moisture was removed using MgSO 4 , distilled under reduced pressure, and concentrated to give 7-(allyloxy)-2-methylheptan-2-ol (82% yield).
  • the monomer mixture was fed at a rate of 500 to 2000 mL/min on a conveyor belt in which a belt having a width of 10 cm and a length of 2 m rotates at a speed of 50 cm/min. Then, the polymerization reaction was performed for 60 seconds by irradiating ultraviolet rays having an intensity of 10 mW/cm 2 simultaneously with the supply of the monomer mixture.
  • the polymer obtained through the polymerization reaction was passed through a hole having a diameter of 10 mm using a meat chopper to prepare a crumb. Subsequently, using an oven capable of up-and-down air volume transfer, hot air at 185°C was flowed from the bottom to the top for 20 minutes, and flowed from the top to the bottom for another 20 minutes to uniformly dry the crumb. .
  • the dried powder was pulverized with a grinder and then classified to obtain a base resin having a size of 150 to 850 ⁇ m.
  • the obtained product was pulverized and classified to obtain a super absorbent polymer having a particle diameter of 150 to 850 ⁇ m.
  • a super absorbent polymer was prepared in the same manner as in Example 3, except that 0.6 g of the crosslinking agent of Example 2 was used instead of the crosslinking agent of Example 1 as an internal crosslinking agent.
  • a super absorbent polymer was prepared in the same manner as in Example 3, except that 0.6 g of the crosslinking agent of Example 3 was used instead of the crosslinking agent of Example 1 as an internal crosslinking agent.
  • a super absorbent polymer was prepared in the same manner as in Example 3, except that 0.6 g of the crosslinking agent of Example 4 was used instead of the crosslinking agent of Example 1 as an internal crosslinking agent.
  • Super absorbent polymer 2 was prepared in the same manner as in Example 3, except that 0.6 g of 3-methylbutane-1,3-diyl diacrylate was used instead of the crosslinking agent of Example 1 as an internal crosslinking agent.
  • the structure of 3-methylbutane-1,3-diyl diacrylate is as follows.
  • the main volatility generated after heating the superabsorbent polymers of Examples 3 and 4 and Comparative Examples at 80° C. is to evaluate whether volatile substances and decomposition products are generated due to thermal decomposition.
  • the amounts of substances and decomposition products generated were measured by HS-GC/MS and are shown in Table 1 below.
  • Example 5 Example 6
  • Example 7 Example 8 Comparative Example 1 MeOH + C4 - - - - 1.6 2-Methyl-1,3-Butadiene 6.4 - - - 82.3 2-Methyl-3-Buten-2-ol - - - - 2.2 3-Methyl-3-Buten-1-ol - - - - 7.8
  • Examples 3 to 8 which are super absorbent polymers prepared using the crosslinking agent compound of the present invention, major volatile substances generated compared to Comparative Example 1 using a material having acrylate at both ends as a crosslinking agent There were remarkably few kinds of degradation products or were not detected at all.
  • the total amount of volatile substances and decomposition products generated in each example was less than 10% of Comparative Example 1, and it was found that one embodiment of the present invention is far superior in terms of generating volatile substances and decomposition products.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un nouveau composé de réticulation et un polymère préparé à l'aide de celui-ci. Plus spécifiquement, la présente invention concerne un nouveau composé de réticulation et un polymère préparé à l'aide de celui-ci, le nouveau composé de réticulation ne subissant pas de pyrolyse au niveau d'une extrémité latérale de celui-ci pour empêcher la génération d'une substance volatile et d'un produit de décomposition à l'avance.
PCT/KR2020/007393 2019-06-10 2020-06-08 Nouveau composé de réticulation et polymère préparé à l'aide de celui-ci WO2020251227A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2021530769A JP7139016B2 (ja) 2019-06-10 2020-06-08 新規な架橋剤化合物およびこれを用いて製造される重合体
US17/271,802 US20210324174A1 (en) 2019-06-10 2020-06-08 Novel Cross-Linking Compound and Polymer Using the Same
EP20822857.7A EP3819334B1 (fr) 2019-06-10 2020-06-08 Nouveau composé de réticulation et polymère préparé à l'aide de celui-ci
CN202080004400.3A CN112533891B (zh) 2019-06-10 2020-06-08 新的交联化合物和使用其的聚合物

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20190068111 2019-06-10
KR10-2019-0068111 2019-06-10
KR10-2020-0065291 2020-05-29
KR1020200065291A KR102495827B1 (ko) 2019-06-10 2020-05-29 신규한 가교제 화합물 및 이를 이용하여 제조되는 중합체

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08165269A (ja) * 1994-10-11 1996-06-25 Daicel Chem Ind Ltd 新規なアルケニル基含有（メタ）アクリレート及びその製造方法
JP2008522003A (ja) 2004-12-03 2008-06-26 ストックハウゼン ゲーエムベーハー 高吸水性ポリマー用架橋剤
KR101442284B1 (ko) * 2006-10-20 2014-09-22 제온 코포레이션 중합성 조성물, 가교성 수지, 및 그것의 제법, 그리고 용도
KR20150090078A (ko) * 2012-10-26 2015-08-05 와코 쥰야꾸 고교 가부시키가이샤 리튬 전지용 결착제, 전극 제작용 조성물 및 전극
KR20150143610A (ko) * 2013-04-15 2015-12-23 쓰리엠 이노베이티브 프로퍼티즈 컴파니 (메트)아크릴레이트 기 및 올레핀 기를 갖는 가교결합제를 포함하는 접착제 및 방법
KR20160145672A (ko) * 2014-04-21 2016-12-20 와코 쥰야꾸 고교 가부시키가이샤 리튬전지용 결착제

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08165269A (ja) * 1994-10-11 1996-06-25 Daicel Chem Ind Ltd 新規なアルケニル基含有（メタ）アクリレート及びその製造方法
JP2008522003A (ja) 2004-12-03 2008-06-26 ストックハウゼン ゲーエムベーハー 高吸水性ポリマー用架橋剤
KR101442284B1 (ko) * 2006-10-20 2014-09-22 제온 코포레이션 중합성 조성물, 가교성 수지, 및 그것의 제법, 그리고 용도
KR20150090078A (ko) * 2012-10-26 2015-08-05 와코 쥰야꾸 고교 가부시키가이샤 리튬 전지용 결착제, 전극 제작용 조성물 및 전극
KR20150143610A (ko) * 2013-04-15 2015-12-23 쓰리엠 이노베이티브 프로퍼티즈 컴파니 (메트)아크릴레이트 기 및 올레핀 기를 갖는 가교결합제를 포함하는 접착제 및 방법
KR20160145672A (ko) * 2014-04-21 2016-12-20 와코 쥰야꾸 고교 가부시키가이샤 리튬전지용 결착제

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