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WO2019039879A2 - Composition de plastifiant composite, procédé de préparation associé et composition de résine polymère l'utilisant - Google Patents

Composition de plastifiant composite, procédé de préparation associé et composition de résine polymère l'utilisant Download PDF

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Publication number
WO2019039879A2
WO2019039879A2 PCT/KR2018/009705 KR2018009705W WO2019039879A2 WO 2019039879 A2 WO2019039879 A2 WO 2019039879A2 KR 2018009705 W KR2018009705 W KR 2018009705W WO 2019039879 A2 WO2019039879 A2 WO 2019039879A2
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Prior art keywords
formula
compound
weight
chemical formula
mixture
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Ceased
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PCT/KR2018/009705
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English (en)
Korean (ko)
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WO2019039879A3 (fr
Inventor
이종화
김영관
정종환
위성유
김장수
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AEKYUNGPETROCHEMICAL Co Ltd
Original Assignee
AEKYUNGPETROCHEMICAL Co Ltd
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Priority claimed from KR1020180032488A external-priority patent/KR102108875B1/ko
Application filed by AEKYUNGPETROCHEMICAL Co Ltd filed Critical AEKYUNGPETROCHEMICAL Co Ltd
Publication of WO2019039879A2 publication Critical patent/WO2019039879A2/fr
Publication of WO2019039879A3 publication Critical patent/WO2019039879A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • C08K5/05—Alcohols; Metal alcoholates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L27/00—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 a halogen; Compositions of derivatives of such polymers
    • C08L27/02—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L27/04—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 a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
    • C08L27/06—Homopolymers or copolymers of vinyl chloride

Definitions

  • the present invention relates to a composite plasticizer composition, a method for producing the same, and a polymer resin composition using the same.
  • Polymer resins are used in a variety of fields such as various household goods, clothing, electric and electronic, automobile, civil engineering, and construction depending on physical properties.
  • Examples of such a polymer resin include polyethylene (PE), polypropylene (PP), polystyrene (PP), polyurethane (PU), and polyvinyl chloride (PVC).
  • the double polyvinyl chloride resin has hard or soft characteristics, is excellent in molding processability, is excellent in price competitiveness, and is applied to various applications with general utility.
  • the polyvinyl chloride resin can not be used alone, but is mixed with a plasticizer for various properties.
  • the plasticizer imparts flexibility to the polyvinyl chloride resin and improves physical properties such as processability.
  • Such a plasticizer when applied to various polymer resins including polyvinyl chloride resin, should be capable of satisfying various physical properties such as good compatibility with resins, excellent plasticization efficiency, low volatility, Depending on the characteristics required.
  • plasticizer In general, the larger the molecular weight of the plasticizer is, the better the aging resistance is, but the compatibility with the resin is lowered, and it tends to be difficult to realize various required properties in a balanced manner. Therefore, in order to meet various physical properties or limited use of plasticizers, a variety of plasticizers have been applied to promote research and development in the direction of increasing plasticization efficiency.
  • the plasticizer in the manufacturing process of applying the plasticizer to the resin or using the final product manufactured using the resin, the plasticizer should be capable of maintaining excellent physical properties at a high temperature or a low temperature at a room temperature. That is, it is required to be able to realize long-term durability, quality stability and reliability by being able to realize excellent resistance to aging in various temperature ranges including heat resistance and cold resistance.
  • An object of the present invention is to provide an environmentally friendly plasticizer composition capable of improving mechanical properties such as tensile strength and elongation as well as heat resistance, cold resistance and aging resistance, and a polymer resin composition containing the same.
  • One aspect of the present invention to attain the above object is a process for producing 2-ethyl-1-hexanol, isononyl alcohol, 2-propyl-1-heptyl alcohol (b) a phthalate derivative mixture (a) which is a reaction product of phthalic acid and a phthalic acid and a compound (b) of the following general formula (1).
  • the phthalic acid is selected from terephthalic acid and isophthalic acid
  • the phthalate derivative mixture derived therefrom is a terephthalate derivative mixture or a mixture of isophthalate derivatives.
  • R 1 to R 3 are each independently C 6 to C 12 alkyl.
  • the phthalate derivative mixture may be a mixture of terephthalate derivatives or a mixture of isophthalate derivatives represented by the following formulas (8) to (13) have.
  • the terephthalate derivative mixture may contain 1 to 40 wt% of the compound of Formula 2, 1 to 50 wt% of the compound of Formula 3, 1 to 50 wt% of the compound of Formula 4, 1 to 40% by weight of the compound of the formula (5), 1 to 40% by weight of the compound of the formula (6) and 1 to 40% by weight of the compound of the formula (7), wherein the isophthalate derivative mixture contains 1 to 40 1 to 50% by weight of the compound of the formula (9), 1 to 50% by weight of the compound of the formula (10), 1 to 40% by weight of the compound of the formula (11), 1 to 40% %. ≪ / RTI >
  • the weight ratio of the phthalate derivative mixture to the compound of Formula 1 may be 1: 9 to 9: 1.
  • R 1 to R 3 are each independently C 6 to C 12 alkyl, more preferably the alkyl is C 8 to C 10 . In the above range, it is more effective in improving the mechanical properties, heat resistance, cold resistance and aging resistance, but is not necessarily limited thereto.
  • the phthalate derivative mixture may contain 1 to 50% by weight of 2-ethyl-1-hexanol, 1 to 70% by weight of isononyl alcohol, -Heptyl alcohol and 1 to 70% by weight of heptyl alcohol with phthalic acid.
  • Another aspect of the present invention is to provide a resin composition comprising the composite plasticizer composition and the polymer resin.
  • the polymer resin may include one or more selected from the group consisting of a polyvinyl chloride resin, a polyolefin resin, a polyester resin, an ABS resin, and an acrylic resin.
  • the resin composition according to one embodiment of the present invention may further include at least one component selected from the group consisting of fillers, lubricants, stabilizers, foaming agents, viscosity regulators, processing aids and dispersants.
  • Another aspect of the present invention is to provide a molded article produced from the above resin composition.
  • the composite plasticizer composition according to the present invention is harmless to the human body and environmentally friendly, and has excellent properties in terms of mechanical properties such as tensile strength and elongation, and further has an advantage of improving heat resistance, cold resistance and aging resistance.
  • the present invention can provide excellent physical properties such as mechanical strength, heat resistance, cold resistance, aging resistance, processability, and long-term durability by mixing the composite plasticizer composition with a polymer resin, It is possible to secure the quality stability and reliability of the finished resin product.
  • " phthalic acid " in the present invention includes terephthalic acid or isophthalic acid, and a " phthalate-based derivative mixture " derived therefrom by reaction with a specific alcohol, Phthalate derivative mixture or a mixture of isophthalate derivatives.
  • the present inventors have intensified researches on plasticizers which can be applied to polymer resins such as polyvinyl chloride resins and satisfy various physical properties requirements that are increasing.
  • the inventors of the present invention have found that they are excellent in physical properties balance and are not limited to low temperature or high temperature
  • a plasticizer having excellent heat resistance, cold resistance and aging resistance has been developed.
  • a composite plasticizer composition comprising a combination of a phthalate derivative mixture, which is a reaction product of a specific component of alcohol and phthalic acid, and a specific citrate compound at the same time is superior in physical properties including synergy with heat resistance and aging resistance, And the present invention has been completed.
  • One embodiment of the present invention relates to a phthalate derivative mixture obtained from the reaction of a specific alcohol component of 2-ethyl-1-hexanol, isononyl alcohol and 2-propyl-1-heptyl alcohol with phthalic acid and a compound represented by the following formula , And to provide a polymer resin composition capable of improving various physical properties including excellent heat resistance, cold resistance and aging resistance by using the composite plasticizer composition.
  • R 1 to R 3 are each independently C 6 to C 12 alkyl.
  • the compound of the formula (1) is an ester compound of citric acid and a C 6 to C 12 alcohol. Although it is not limited theoretically, the combination of the phthalate derivative mixture improves cold resistance and heat resistance and further enhances the aging resistance at a high temperature It can be improved.
  • R 1 to R 3 each independently represent C 6 to C 12 alkyl, wherein any one of R 1 to R 3 has a long chain of C 6 to C 12 alkyl It is more effective in improving the thermal resistance of cold resistance and heat resistance without deteriorating physical properties and at the same time improving the aging resistance. That is, when all of R 1 to R 3 are simultaneously C 6 to C 12 alkyl long chains, the present invention is more effective in achieving the desired physical properties.
  • R 1 to R 3 are each independently C 8 to C 10 alkyl.
  • R 1 to R 3 are each independently C 8 to C 10 alkyl.
  • the compound represented by Formula 1 may be, for example, a trihexyl citrate, a triheptyl citrate, a triethylhexyl citrate, a triisononyl citrate, triisononyl citrate, triisodecyl citrate, tripropylheptyl citrate, tridodecyl citrate and trioctyl dodecyl citrate from the group consisting of triisononyl citrate, triisodecyl citrate, tripropylheptyl citrate, tridodecyl citrate and trioctyl dodecyl citrate. And any one or more selected, but not limited thereto.
  • At least one selected from triethyl hexylate, triisononyl citrate, triisodecyltreate, tripropylheptyl citrate, tridodecyltreate and trioctyldodecyltreate is used has an effect of further improving heat resistance, cold resistance and aging resistance when applied to a polymer resin composition.
  • the compound represented by the formula (1) may be a commercial product or an esterified product of citric acid and a C 6 to C 12 alcohol.
  • the phthalate derivative mixture may be a terephthalate derivative compound or an isophthalate derivative compound.
  • the terephthalate derivative mixture or the isophthalate derivative mixture is characterized in that different types of terephthalate derivative components or isophthalate derivative components are mixed, respectively.
  • the phthalate derivative mixture may be an isophthalate derivative comprising at least one selected from the group consisting of terephthalate derivative mixtures containing at least one of the following compounds (2) to (7) And mixtures thereof.
  • the terephthalate derivative mixture is a mixture of the above formulas 2, 3 and 5; The mixture of Formulas 3, 4, and 7; And mixtures of the above formulas (2), (4) and (6);
  • the isophthalate derivative mixture may be a mixture of the above formulas (8), (9) and (11); A mixture of the above formulas (9), (10) and (13); And a mixture of the above formulas (8), (9) and (11); , But the present invention is not limited thereto.
  • each of the compounds may be controlled within a range that achieves the desired physical properties.
  • the content of each compound may be 1 to 50 wt%, preferably 5 to 40 wt% , But are not necessarily limited thereto.
  • the terephthalate derivative mixture may comprise a combination of compounds of the following formulas 2 to 7, and the isophthalate derivative mixture may comprise a combination of compounds of formulas 8 to 13: This is because the terephthalate derivative mixture or the isophthalate derivative mixture has more effective characteristics in terms of improvement of physical properties such as workability, heat loss, heat resistance, cold resistance, aging resistance and weather resistance and balance of physical properties.
  • the terephthalate derivative mixture comprises 1 to 40% by weight of the compound of Formula 2, 1 to 50% by weight of the compound of Formula 3, 1 to 50% by weight of the compound of Formula 4, 1 to 40% by weight of the compound of the formula (6) and 1 to 40% by weight of the compound of the formula (7), wherein the isophthalate derivative mixture comprises 1 to 40% by weight of the compound of the formula 1 to 40% by weight of the compound of the formula (11) and 1 to 40% by weight of the compound of the formula (13), 1 to 50% by weight of the compound .
  • the isophthalate derivative mixture comprises 2 to 30% by weight of the compound of the formula 8, 5 to 40% by weight of the compound of the formula 9, 10 to 40% by weight of the compound of the formula 10, 5 to 30% by weight, the compound of the formula 12 is 5 to 30% by weight, and the compound of the formula 13 is 10 to 30% by weight.
  • the isophthalate derivative mixture may contain 2 to 30% by weight of the compound of Formula 8, 5 to 40% by weight of the compound of Formula 9, 10 to 40% by weight of the compound of Formula 10, 5 to 30% 5 to 30% by weight of the compound of the formula (12) and 10 to 30% by weight of the compound of the formula (13).
  • the phthalate derivative mixture may have a weight mixing ratio with the compound of Formula 1 of 1: 9 to 9: 1, preferably 2: 8 to 8: 2, more preferably 3: 7 to 7: 3 have.
  • the plasticizer applied to the polymer resin has the characteristics of being able to achieve the same level or better mechanical properties while maintaining various physical property balance and at the same time improving the aging resistance at high temperature.
  • Another embodiment of the present invention is a process for synthesizing a phthalate derivative mixture by reacting a reaction solution comprising 2-ethyl-1-hexanol, isononyl alcohol and 2-propyl-1-heptyl alcohol, terephthalic acid or phthalic acid of isophthalic acid And mixing the synthesized phthalate derivative mixture with a compound of the following general formula (1).
  • R 1 to R 3 are each independently C 6 to C 12 alkyl.
  • the phthalate derivative mixture comprises 1 to 50% by weight of 2-ethyl-1-hexanol, 1 to 70% by weight of isononyl alcohol and 1 to 70% by weight of 2-propyl- May be obtained by esterification reaction of a mixed alcohol component with any phthalic acid selected from terephthalic acid and isophthalic acid.
  • the step of synthesizing the phthalate derivative mixture is carried out by adding 0.2 to 0.5 mol of 2-ethyl-1-hexanol, 0.4 to 2 mol of isononyl alcohol to 1 mol of phthalic acid, i.e., terephthalic acid or isophthalic acid, 0.8 mol of 2-propyl-1-heptyl alcohol and 0.8 to 1.2 mol of 2-propyl-1-heptyl alcohol.
  • a mixture of terephthalate derivatives comprising a mixture of compounds of the following formulas (2) to (7) or a mixture of isophthalate derivatives of the following formulas (8) to (13) is obtained through the reaction of phthalic acid with alcohol components in the above- And has effective properties in terms of process efficiency and processability within the above-mentioned molar range, but the molar range is not limited to the above-mentioned numerical range, but is a non-limiting example.
  • the various ester compounds obtained through the esterification reaction using an acid and an alcohol as raw materials may have various properties depending on the kind of the reactants, the molar ratio, the reaction temperature, and the like.
  • the specific alcohol component according to the present invention and the molar ratios of these components The phthalate derivative components obtained according to the reaction of phthalic acid can further improve the plasticizer performance in combination with the compound of Formula 1 in the complex plasticizer composition.
  • the terephthalate derivative mixture obtained through the above-mentioned synthesis step may contain 1 to 40% by weight of the following compound (2), 1 to 50% by weight of the compound of the formula (3), 1 to 50% by weight of the compound of the formula (4) 40% by weight of the compound of the formula (6), and 1 to 40% by weight of the compound of the formula (7).
  • the isophthalate derivative mixture obtained through the above-mentioned synthesis step may contain 1 to 40% by weight of the following compound (8), 1 to 50% by weight of the compound of the formula (9), 1 to 50% by weight of the compound of the formula 1 to 40% by weight of the compound of the formula (12) and 1 to 40% by weight of the compound of the formula (13).
  • the esterification reaction of the alcohol components and the phthalic acid may be carried out under conventional esterification reaction conditions, preferably at 180 to 250 ° C for 6 to 20 hours, but is not limited thereto.
  • the weight ratio of the phthalate derivative mixture to the compound of Formula 1 may be 1: 9 to 9: 1, preferably 2: 8 to 8: 2, more preferably 3: 7 to 7: 3 .
  • the polymer resin may include at least one selected from the group consisting of a polyvinyl chloride resin, a polyolefin resin, a polyester resin, an ABS resin, and an acrylic resin, and is preferably a polyvinyl chloride Resin.
  • the polymeric resin composition according to one embodiment of the present invention includes the composite plasticizer composition of the present invention and is capable of realizing excellent physical properties at high temperature or low temperature and further improving the aging resistance at high temperature.
  • the polymer resin composition according to one embodiment of the present invention may contain 10 to 150 parts by weight, preferably 20 to 140 parts by weight, more preferably 30 to 120 parts by weight, based on 100 parts by weight of the polymer resin, of the composite plasticizer composition have.
  • the desired physical properties of the present invention are more effective in terms of improvement of heat resistance, cold resistance and aging resistance, but this is a non-limiting example and is not limited to the above numerical range.
  • the polymer resin composition may further include at least one selected from the group consisting of a secondary plasticizer, a stabilizer, a filler, a lubricant, a flame retardant, a viscosity regulator, a foaming agent, a promoter and a pigment.
  • the additive is not particularly limited, but may be added in an amount of 0.1 to 10 parts by weight, more preferably 1 to 5 parts by weight, based on 100 parts by weight of the polymer resin. Within this range, each additive can achieve the desired effect.
  • Still another aspect of the present invention is to provide a molded article produced from the above-described polymer resin composition.
  • the molded article may be a wallpaper, a compound, a wire compound, a sheet, a film, a tarpaulin, a hose, a shoe, a sealant, an office supplies, a glove, a bottle cap, a mat, a gasket, a food packaging material, , Electric machine parts, and the like.
  • the tensile strength was measured when the specimen was stretched 100% by tension. This means that the plasticization efficiency is better, and the lower the 100% modulus value, the better the plasticization efficiency of the material.
  • the specimen was aged in an oven (Geer Oven) at 113 DEG C for 168 hours, and then calculated as a value of (elongation of specimen after aging / elongation of specimen before aging) x100. At this time, when the resultant value is close to 100, it means that mechanical properties similar to those before aging are exhibited.
  • the tensile strength of the specimens was measured in accordance with KS M 3156.
  • the specimens were aged in an oven (Geer Oven) at 113 ° C for 168 hours and then calculated as the value of (weight of test piece after aging / weight of test piece before aging) ⁇ 100.
  • the resultant terephthalate derivative mixture was analyzed by a GC-Mass analyzer. As a result, it was found that the weight percentage of the terephthalate derivative mixture was 5: 10: 30: 10: 15: 30.
  • TEHC triethylhexyl citrate
  • Example 1 The same procedure was followed as in Example 1, except that the amounts of the alcohol compound components were varied in Example 1 and the proportions of the respective compounds in the terephthalate derivative mixture were changed as shown in Table 1 below.
  • Example 1 The same procedure as in Example 1 was carried out except that tributyl citrate (TBC) was used instead of triethylhexitrate in Example 1.
  • TBC tributyl citrate
  • the terephthalate derivative mixture thus obtained was analyzed by a GC-Mass analyzer. As a result, it was found that the weight percentage of the terephthalate derivative mixture was 4: 11: 25: 11: 14: 35.
  • TEHC triethylhexyl citrate
  • Example 2 The same procedure as in Example 1 was carried out except that the amounts of the alcohol compound components were varied in Example 10 and the proportions of the respective compounds in the terephthalate derivative mixture were changed as shown in Table 2 below.
  • Example 1 The procedure of Example 1 was repeated, except that tributyl citrate was used instead of triethylhexitrate in Example 10.
  • Example 1 The procedure of Example 1 was repeated, except that di (2-propylheptyl) phthalate was used instead of triethylhexitrate in Example 10.
  • Example 1 The procedure of Example 1 was repeated, except that diisodecyl phthalate (DIDP) was used instead of the composite plasticizer composition as a plasticizer in Example 19.
  • DIDP diisodecyl phthalate
  • the examples using the composite plasticizer composition in which the terephthalate derivative mixture or the isophthalate derivative mixture according to the present invention and TEHC were mixed showed excellent tensile strength and durability when compared with the commercial plasticizer DIDP It was confirmed that the mechanical properties of elongation as well as heat resistance, cold resistance and further aging resistance were remarkably improved.
  • the examples according to the present invention in the case of Comparative Examples 5 and 7 using tributyl citrate instead of triethylhexitrate or Comparative Examples 6 and 8 using a diaphthalate compound, the aging resistance was significantly lowered , And it was confirmed that heat resistance and cold resistance at high temperature were not good.

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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

La présente invention concerne une composition de plastifiant composite respectueuse de l'environnement permettant d'améliorer non seulement des propriétés mécaniques, telles que la résistance à la traction et à l'allongement, mais également une résistance à la chaleur, une résistance au froid et une résistance au vieillissement, l'invention concernant également un procédé de préparation associé, et une composition de résine polymère l'utilisant.
PCT/KR2018/009705 2017-08-25 2018-08-23 Composition de plastifiant composite, procédé de préparation associé et composition de résine polymère l'utilisant Ceased WO2019039879A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2017-0107882 2017-08-25
KR20170107882 2017-08-25
KR1020180032488A KR102108875B1 (ko) 2017-08-25 2018-03-21 복합 가소제 조성물, 이의 제조방법 및 이를 이용한 고분자 수지 조성물
KR10-2018-0032488 2018-03-21

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WO2019039879A2 true WO2019039879A2 (fr) 2019-02-28
WO2019039879A3 WO2019039879A3 (fr) 2019-04-25

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113692425A (zh) * 2019-05-02 2021-11-23 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103788406A (zh) * 2014-02-11 2014-05-14 汤宁 一种可完全替代dop的生物基环保增塑剂
KR101674317B1 (ko) * 2015-02-12 2016-11-08 주식회사 엘지화학 가소제 조성물, 수지 조성물 및 이들의 제조 방법
KR101907252B1 (ko) * 2015-03-20 2018-10-11 주식회사 엘지화학 가소제 조성물, 수지 조성물 및 이들의 제조 방법
KR20170055360A (ko) * 2015-11-11 2017-05-19 주식회사 엘지화학 가소제 조성물, 수지 조성물 및 이들의 제조 방법
KR101731366B1 (ko) * 2016-09-20 2017-04-28 애경유화주식회사 복합 가소제 조성물, 이의 제조방법, 및 이를 이용한 고분자 수지 조성물

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113692425A (zh) * 2019-05-02 2021-11-23 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物
EP3964543A4 (fr) * 2019-05-02 2022-06-22 Lg Chem, Ltd. Composition de plastifiant et composition de résine la comprenant
CN113692425B (zh) * 2019-05-02 2023-06-30 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物
TWI825312B (zh) * 2019-05-02 2023-12-11 南韓商Ｌｇ化學股份有限公司 塑化劑組成物及含彼之樹脂組成物
US12351700B2 (en) 2019-05-02 2025-07-08 Lg Chem, Ltd. Plasticizer composition and resin composition including the same

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