WO2013031629A1 - Plastifiant polyglycérique pour résines, et composition de résine thermoplastique le contenant - Google Patents

Plastifiant polyglycérique pour résines, et composition de résine thermoplastique le contenant Download PDF

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Publication number
WO2013031629A1
WO2013031629A1 PCT/JP2012/071290 JP2012071290W WO2013031629A1 WO 2013031629 A1 WO2013031629 A1 WO 2013031629A1 JP 2012071290 W JP2012071290 W JP 2012071290W WO 2013031629 A1 WO2013031629 A1 WO 2013031629A1
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WO
WIPO (PCT)
Prior art keywords
thermoplastic resin
polyglycerin
plasticizer
resin
ethylhexanoic acid
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PCT/JP2012/071290
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English (en)
Japanese (ja)
Inventor
保田　亮二
栗山　重平
Original Assignee
阪本薬品工業株式会社
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Publication of WO2013031629A1 publication Critical patent/WO2013031629A1/fr

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    • 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
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/14—Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols

Definitions

  • the present invention relates to a polyglycerin-based resin plasticizer composed of polyglycerin and 2-ethylhexanoic acid, and a thermoplastic resin composition containing the same and having excellent flexibility and bleeding resistance.
  • polyester resins and polylactic acid resins are often used for applications such as containers and packaging materials.
  • polyvinyl butyral resins are used and studied as laminated glass interlayers and solar cell encapsulants for automobiles and buildings, and ionomer resins are used as containers, packaging materials, solar cell encapsulants, etc. ing.
  • plasticizers since these resins lack flexibility when applied to films, sheets and the like, the use of plasticizers has been studied for the purpose of facilitating processing and imparting flexibility to molded products.
  • a highly volatile plasticizer reduces the amount of plasticizer remaining in the resin composition, causing problems in performance and physical properties, and in terms of work environment. But it becomes a problem. Therefore, a plasticizer that satisfies both compatibility and heat resistance has been demanded.
  • JP-A-07-177826 acetylated monoglyceride having an acyl group having 8 to 14 carbon atoms is disclosed in JP-A-2002-053742.
  • Japanese Patent Laid-Open No. 2008-296482 discloses polyglycerin acetate and the like, but none of them is sufficiently satisfactory because of poor heat resistance.
  • JP-A-2000-198908 also discloses phthalic acid derivatives such as dioctyl phthalate, but safety has been pointed out due to problems such as environmental hormones.
  • JP-A-2011-042552 discloses triethylene glycol 2-ethylhexanoic acid ester and the like.
  • JP2009-035699A discloses diglycerin monocaprylate, diglycerin monodistearate, polypropylene glycol and the like.
  • the present invention provides a plasticizer that has excellent heat resistance that does not volatilize even at high temperatures and has good compatibility with the resin, and heat that is excellent in flexibility and bleed resistance. It aims at providing a plastic resin composition.
  • the present inventor has conducted intensive studies, and as a result, a polyglycerin having an average degree of polymerization calculated from a hydroxyl value of 2 to 10 and 2-ethylhexanoic acid is included.
  • the inventors have found that the above problems can be solved by using glycerin 2-ethylhexanoate.
  • a thermoplastic resin composition having a more excellent function can be provided when the solubility parameter (SP value) is 9.0 to 12.5 in the polyglycerin 2-ethylhexanoate. .
  • the glass transition temperature can be efficiently lowered, the melt index can be improved moderately, and bleeding can be achieved under long-term storage conditions. Since it is not seen at all and has excellent compatibility, the desired reforming performance can be maintained for a long time without causing deterioration of performance over time or quality change.
  • the polyglycerol of polyglycerol 2-ethylhexanoate used in the present invention one having an average degree of polymerization of 2 to 10 calculated from the hydroxyl value is used. Moreover, the polyglycerol of this range may be used independently, or 2 or more types may be used together.
  • the average degree of polymerization is the average degree of polymerization (n) of polyglycerin calculated from the hydroxyl value by end group analysis. Specifically, the average degree of polymerization is calculated from the following formulas (Formula 1) and (Formula 2).
  • the hydroxyl value in the above (Formula 2) is a numerical value that is an index of the number of hydroxyl groups contained in polyglycerin, and is free contained in 1 g of polyglycerin.
  • the number of milligrams of potassium hydroxide is calculated according to the Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (I), 2003 edition”.
  • polyglycerol having an average degree of polymerization calculated from the hydroxyl value of 2 to 10 a composition having a molecular weight distribution is generally used except for diglycerol having an average degree of polymerization of 2. Two or more kinds of these polyglycerols having different molecular weight distributions may be mixed. If the average degree of polymerization calculated from the hydroxyl value of the polyglycerol mixture is 2 to 10, the average degree of polymerization is less than 2, and 10 More than polyglycerol can be used.
  • the polyglycerin 2-ethylhexanoic acid ester used in the present invention is composed of 2-ethylhexanoic acid, which is a branched alkanoic acid having 8 carbon atoms, and preferably has a purity of 95% or more.
  • 2-ethylhexanoic acid is octylic acid (manufactured by Kyowa Hakko Chemical Co., Ltd.).
  • the solubility parameter (SP value) of the polyglycerol 2-ethylhexanoic acid ester of the present invention is in the range of 9.0 to 12.5, preferably 9.0 to 11.0, more preferably 9.0. The range is 10.0.
  • the solubility parameter here can be calculated by the method described in “Polymer Engineering and Science, Vol. 14, No. 2, p. 147-154 (1974)” (Fedors method).
  • the total heat of molar evaporation ( ⁇ H) and the total molar volume (V) of atomic groups described in pages 151 to 153 of the above-mentioned document can be used.
  • Those having a close numerical value are easy to mix with each other (high compatibility), and those having a close numerical value are indices that indicate that they are difficult to mix.
  • polyglycerin 2-ethylhexanoic acid ester when the SP value is less than 9.0 or more than 12.5, the compatibility with the resin is lowered and bleeding occurs over time, which is not preferable. .
  • the esterification rate of the polyglycerol 2-ethylhexanoic acid ester of the present invention is preferably 20 mol% or more, more preferably 50 mol% or more. Outside this range, the compatibility with the resin tends to decrease, and the plasticizer may bleed.
  • the esterification rate refers to the average degree of polymerization of polyglycerol (n) calculated from the hydroxyl value by end group analysis, the number of hydroxyl groups of this polyglycerol (n + 2), and 2-addition to polyglycerol.
  • M the number of moles of ethylhexanoic acid
  • the hydroxyl value is a numerical value that is an index of the number of hydroxyl groups contained in polyglycerol, and is required to neutralize acetic acid necessary for acetylating free hydroxyl groups contained in 1 g of polyglycerol.
  • the number of milligrams of potassium hydroxide The number of milligrams of potassium hydroxide is calculated according to the Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (I), 2003 edition”.
  • an average degree of polymerization is an average degree of polymerization (n) of the polyglycerol calculated from the hydroxyl value by a terminal group analysis method.
  • the average degree of polymerization is calculated from the following formulas (Formula 1) and (Formula 2).
  • (Formula 2) hydroxyl value 56110 (n + 2) / molecular weight
  • the polyglycerin 2-ethylhexanoate of the present invention preferably has a weight reduction rate of 5% by weight or less when the temperature is raised from 25 ° C. to 200 ° C. at a rate of 5 ° C. per minute.
  • the weight reduction rate exceeds 5% by weight, the amount of volatilization increases when performing melt-kneading with the thermoplastic resin, and the residual amount of plasticizer in the resin composition decreases, causing problems in performance and physical properties. there is a possibility.
  • problems such as fullness of odor due to volatile components in terms of the working environment, it is necessary to limit to this range.
  • the polyglycerin 2-ethylhexanoate of the present invention is synthesized by a general esterification reaction.
  • the reaction is allowed to proceed while heating to a reaction temperature of 160 ° C. or higher under synthesis conditions equipped with a reflux apparatus and removing the produced water out of the system.
  • the polyglycerin 2-ethylhexanoic acid ester of the present invention can be synthesized without a catalyst or in the presence of a catalyst, and usable catalysts include basic catalysts and acidic catalysts.
  • basic catalyst sodium hydroxide, potassium hydroxide and the like are preferable.
  • acidic catalyst any of (ortho) phosphoric acid, polyphosphoric acid, and acidic phosphoric acid esters such as 2-ethylhexyl acid phosphate, oleyl acid phosphate, stearyl acid phosphate, and the like are preferable. Two or more types may be used in combination.
  • hydrochloric acid sulfuric acid, p-toluenesulfonic acid, stannous chloride, stannic chloride, dibutyltin bis (2-ethylhexanoate), dibutyltin diacetate, tetraethoxytitanium, tetraisopropoxytitanium, etc. Although it is mentioned, it is not limited to these.
  • the present invention also provides the above-mentioned polyglycerin 2-ethylhexanoic acid ester and a thermoplastic resin containing the same.
  • the content ratio of the polyglycerin 2-ethylhexanoic acid ester to be blended as the plasticizer component is preferably 1 to 60 parts by weight and more preferably 3 to 40 parts by weight with respect to 100 parts by weight of the thermoplastic resin. preferable. If the content ratio of polyglycerin 2-ethylhexanoic acid ester is less than 1 part by weight, the plasticizing effect is not sufficiently exerted, and if it exceeds 60 parts by weight, the mechanical properties of the thermoplastic resin composition are lowered. This range is preferred.
  • thermoplastic resin used in the thermoplastic resin composition of the present invention is preferably a polymer having a polar group in its structure.
  • Typical examples include, but are not limited to, polyester resins, polylactic acid resins, polyvinyl butyral resins, ionomer resins, polyvinyl chloride resins, polycarbonate resins, polyamide resins and the like, and resins that combine several of these. is not.
  • the thermoplastic resin composition of the present invention can also contain a plasticizer other than polyglycerin 2-ethylhexanoate.
  • the plasticizer include glycerin fatty acid esters such as glycerin diacetomonocaprylate, glycerin diacetomonolaurate, glycerin 2-ethylhexanoic acid monoester, glycerin 2-ethylhexanoic acid diester, glycerin 2-ethylhexanoic acid triester, And polyethylene glycol fatty acid esters such as triethylene glycol 2-ethylhexanoate, tetraethylene glycol 2-ethylhexanoate, and pentaethylene glycol 2-ethylhexanoate.
  • plasticizers can be used alone or in combination of two or more.
  • the compatibility is excellent and bleed resistance can be maintained over a long period of time.
  • Plasticizers that can be used in the thermoplastic resin composition of the present invention include general plasticizers such as polyester plasticizers represented by dioctyl phthalate, diisononyl phthalate, tributyl acetyl citrate, and adipic acid ester in addition to the above-mentioned ones. Can also be used.
  • thermoplastic resin composition of the present invention various additives such as an antioxidant, an ultraviolet absorber, an infrared absorber, a thermal stabilizer, a light stabilizer, and the like, as long as the object of the present invention is not impaired.
  • a colorant, a foaming agent, a flame retardant, a fluorescent brightening agent, an antistatic agent, a filler, and the like can be appropriately blended.
  • the method for preparing the resin composition of the present invention is not particularly limited, and a conventionally known method can be used.
  • the resin composition can be prepared by a melt kneading method or a method of dissolving and mixing in a solvent.
  • the melt kneading method is preferable.
  • a thermoplastic resin, the polyglycerin 2-ethylhexanoic acid ester of the present invention, and various additives used as desired are blended, and a single-screw extruder, a multi-screw extruder, a kneader It is preferable to melt knead at a temperature of 80 ° C. or higher using a bumper mixer or the like.
  • thermoplastic resin composition of the present invention glass transition temperature (Tg) and melt index (MI value) can be used.
  • Tg glass transition temperature
  • MI value melt index
  • the glass transition temperature is preferably lowered as compared with the case where no plasticizer is contained, and the greater the reduction width, the higher the flexibility imparting effect.
  • the melt index is preferably increased as compared with the case where no plasticizer is contained, and it is desired that the melt index has a moderate increase range.
  • the suitable range of each numerical value changes with kinds and uses of resin.
  • the polyglycerin used in this synthesis is diglycerin, triglycerin, tetraglycerin, hexaglycerin, and decaglycerin (both manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), and the average degree of polymerization calculated from the hydroxyl value is They are 2, 3, 4, 6, 10 respectively.
  • octylic acid manufactured by Kyowa Hakko Chemical Co., Ltd.
  • polyvinyl butyral resin, polylactic acid resin, and ethylene ionomer resin were used as the thermoplastic resin. Examples of the present invention and comparative examples are shown below. However, “%” is based on weight unless otherwise specified.
  • the glass transition temperature (Tg) was measured using the differential scanning calorimeter (Thermo Plus DSC8320, product made by RIGAKU). Weigh 5 mg each of the sample and ⁇ -alumina as a control substance in an aluminum sample cell, raise the temperature from room temperature to 200 ° C. at a rate of 5 ° C. per minute in a nitrogen atmosphere, and then increase to ⁇ 50 ° C. at a rate of 5 ° C. per minute.
  • the glass transition temperature is obtained from the intersection of the tangent line of the endothermic curve and the extension line of the baseline when the temperature is raised to 200 ° C at a rate of 5 ° C per minute. It was.
  • the glass transition temperature of the thermoplastic resin containing no polyglycerin 2-ethylhexanoate of the present invention was 75 ° C. for polyvinyl butyral resin, 60 ° C. for polylactic acid resin, and 95 ° C. for ethylene ionomer resin.
  • MI value melt index value
  • MELT INDEXER TYPE C-5059D made by Toyo Seiki Seisakusho. Measurement was performed in accordance with JIS K-7210 under the conditions of 10.0 g of a sample, a preheating time of 360 seconds, a test time of 600 seconds, a test temperature of 190 ° C., a test load of 2.16 kgf, and method A (CUTT OFF method).
  • the melt index of the thermoplastic resin containing no polyglycerol 2-ethylhexanoate of the present invention is 5.5 g / 10 min for polyvinyl butyral resin, 9.4 g / 10 min for polylactic acid resin, and 10 for ethylene ionomer resin. 0.0 g / 10 min.
  • thermoplastic resin composition was visually evaluated for the presence or absence of bleeding of the plasticizer when left at 25 ° C. for 1 month and then at 10 ° C. for 1 month. No bleed at 25 ° C. or 10 ° C., no bleed at 25 ° C., slightly bleed at 10 ° C., no bleed at 25 ° C., 10 ° C. The case where bleeding occurred was evaluated as ⁇ , and the case where plasticizer bleeding occurred at 25 ° C. was evaluated as ⁇ . Then, the evaluated thermoplastic resin composition was judged as a preferred example.
  • polyglycerin 2-ethylhexanoic acid ester (abbreviation: 2G2EH) was obtained.
  • 30.0 g of the obtained polyglycerin 2-ethylhexanoic acid ester was added to 100.0 g of the polyvinyl butyral resin, and melt kneading was carried out at 190 ° C. using a twin-screw extruder to obtain polyvinyl butyral.
  • a resin composition was obtained.
  • the resin composition had a Tg of 10 ° C. and a melt index of 28.0 g / 10 min, and no plasticizer bleed was observed at either 10 ° C. or 25 ° C.
  • Example 1 30.0 g of polyglycerin 2-ethylhexanoic acid ester (abbreviation: 2G2EH) obtained in Synthesis Example 1 is added to 100.0 g of polyvinyl butyral resin, and melt-kneaded at 190 ° C. using a twin screw extruder.
  • the polyvinyl butyral resin composition was obtained by performing.
  • the resin composition had a Tg of 10 ° C. and a melt index of 28 g / 10 min. No plasticizer bleed was observed at any of 10 ° C. and 25 ° C., and the evaluation was good.
  • thermoplastic resin composition was prepared and evaluated in the same manner as in Example 1 except that the type of thermoplastic resin and the type and amount of plasticizer were changed. The obtained results are shown in Tables 3 and 4.
  • thermoplastic resin to which a polyglycerin fatty acid ester composed of polyglycerin having an average degree of polymerization calculated from a hydroxyl value of 2 to 10 and 2-ethylhexanoic acid is added, and the polyglycerin fatty acid ester And glycerin 2-ethylhexanoic acid ester and polyethylene glycol 2-ethylhexanoic acid ester, or the polyglycerin fatty acid ester and glycerin 2-ethylhexanoic acid ester, or the polyglycerin fatty acid ester and polyethylene glycol 2-ethylhexanoic acid ester,
  • the glass transition temperature can be efficiently reduced, and the melt index can be increased moderately, and further, no bleed is seen under long-term storage conditions, performance deterioration with time, Without causing quality change was found to be maintained for a long period of time the desired reforming performance.
  • the polyglycerin skeleton is controlled by using a polyglycerin having an average degree of polymerization of 2 to 10 to a specific esterification rate or a specific SP value. It is considered that the polarity of the ether bond portion in the inside influences and shows excellent compatibility with a thermoplastic resin partially having a polar group and a modification effect.
  • the glass transition temperature can be efficiently lowered, the melt index can be increased moderately, and bleeding can be achieved under long-term storage conditions. Since it is not seen at all and has excellent compatibility, it can maintain desired reforming performance for a long time without causing deterioration of performance over time or quality change, and various films / sheets, plastic molding It can be applied in applications such as goods.

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Cette invention concerne un plastifiant pour résines, qui n'est pas volatil à températures élevées et fait preuve d'une excellente résistance à la chaleur et d'une bonne compatibilité avec les résines. Il peut être obtenu à l'aide d'un ester d'acide 2-éthylhexanoïque de polyglycérol, ledit ester d'acide 2-éthylhexanoïque de polyglycérol étant constitué d'un acide 2-éthylhexanoïque et d'un polyglycérol ayant un degré moyen de polymérisation, calculé à partir de l'indice d'hydroxyle, de deux à dix, et ayant un paramètre de solubilité (valeur SP) de 9,0 à 12,5. De plus, une composition de résine thermoplastique ayant une excellente flexibilité et résistance au suintement peut être obtenue.
PCT/JP2012/071290 2011-08-30 2012-08-23 Plastifiant polyglycérique pour résines, et composition de résine thermoplastique le contenant WO2013031629A1 (fr)

Applications Claiming Priority (4)

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JP2011186737 2011-08-30
JP2011-186737 2011-08-30
JP2012104287 2012-04-30
JP2012-104287 2012-04-30

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014147841A1 (fr) * 2013-03-22 2014-09-25 株式会社クラレ Composition ayant une excellente transparence

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6469377B2 (ja) * 2014-07-15 2019-02-13 阪本薬品工業株式会社 ポリグリセリン系樹脂可塑剤、及びそれを含有するセラミックスラリー組成物、並びにセラミック成形体

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JP2002201362A (ja) * 2000-12-27 2002-07-19 Matsumoto Yushi Seiyaku Co Ltd 帯電防止性樹脂組成物
JP2008195808A (ja) * 2007-02-13 2008-08-28 Sakamoto Yakuhin Kogyo Co Ltd 反応性希釈剤およびそれを用いたポリウレタン組成物
JP2009096942A (ja) * 2007-10-19 2009-05-07 Sakamoto Yakuhin Kogyo Co Ltd 反応性希釈剤を含有するポリウレタン塗料組成物

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JP2010195717A (ja) * 2009-02-25 2010-09-09 Sakamoto Yakuhin Kogyo Co Ltd 低酸価、且つ低水酸基価の多価アルコール脂肪酸エステルの製造方法

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Publication number Priority date Publication date Assignee Title
JP2002201362A (ja) * 2000-12-27 2002-07-19 Matsumoto Yushi Seiyaku Co Ltd 帯電防止性樹脂組成物
JP2008195808A (ja) * 2007-02-13 2008-08-28 Sakamoto Yakuhin Kogyo Co Ltd 反応性希釈剤およびそれを用いたポリウレタン組成物
JP2009096942A (ja) * 2007-10-19 2009-05-07 Sakamoto Yakuhin Kogyo Co Ltd 反応性希釈剤を含有するポリウレタン塗料組成物

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014147841A1 (fr) * 2013-03-22 2014-09-25 株式会社クラレ Composition ayant une excellente transparence
JP5632077B1 (ja) * 2013-03-22 2014-11-26 株式会社クラレ 透明性に優れる組成物
US10519295B2 (en) 2013-03-22 2019-12-31 Kuraray Co., Ltd. Composition having excellent transparency

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