WO2010030085A2 - 가소제 및 이를 포함한 폴리염화비닐 수지 조성물 - Google Patents
가소제 및 이를 포함한 폴리염화비닐 수지 조성물 Download PDFInfo
- Publication number
- WO2010030085A2 WO2010030085A2 PCT/KR2009/004841 KR2009004841W WO2010030085A2 WO 2010030085 A2 WO2010030085 A2 WO 2010030085A2 KR 2009004841 W KR2009004841 W KR 2009004841W WO 2010030085 A2 WO2010030085 A2 WO 2010030085A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- plasticizer
- polyvinyl chloride
- carbon atoms
- chloride resin
- present
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- 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
-
- 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
Definitions
- the present invention relates to an ester compound and a plasticizer for plastics, in particular polyvinyl chloride (PVC), including the same, and more specifically, to polyvinyl chloride resin having excellent plasticization efficiency and improved physical properties such as hardness and tensile strength. It relates to an ester plasticizer using an esterification reaction of 1,4-butanediol with various carboxylic acids to enable the preparation of the composition.
- PVC polyvinyl chloride
- Polyvinyl chloride resin is a homopolymer of vinyl chloride or a hybrid polymer containing 50% or more of vinyl chloride, and is a general-purpose resin that can be used by processing methods such as extrusion, injection molding, calendering, and the like. It is widely used in various products such as electric wires, electromechanical products, toys, films, sheets, artificial leather, tarpaulins, tapes, food packaging materials, and medical supplies. Such a polyvinyl chloride resin may impart various processing properties by appropriately adding various additives such as plasticizers, stabilizers, fillers, and pigments.
- the plasticizer is an essential additive that is added to the polyvinyl chloride resin to impart various physical properties and functions such as processability, flexibility, electrical insulation, and adhesiveness.
- Low volatility is a very important factor for plasticizers, which is important both during incorporation into plastic compositions and during actual use of molded articles.
- plasticizers provided for application in the food and beverage sector and in the pharmaceutical sector shall be harmless to health.
- Representative kinds of such plasticizers include phthalates.
- phthalates due to controversy over regenerative toxicity under legislation already regulating toxic substances, the use of phthalates is expected to decrease significantly in the future. Therefore, there is a demand for the development of a plasticizer having a plasticization efficiency equivalent to that of a phthalate-based plasticizer while having an ester-based material containing no phthalate.
- an object of the present invention is to provide a novel ester plasticizer compound using 1,4-butanediol having physical properties equivalent to or superior to those of conventional phthalate plasticizers.
- Another object of the present invention is to provide a plasticizer composition comprising the novel ester plasticizer.
- Another object of the present invention is to provide a polyvinyl chloride resin containing the novel plasticizer compound.
- Plasticizer according to the first aspect of the present invention for achieving the above technical object as an ester compound represented by the following formula (1),
- R 1 is a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms
- R 2 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
- Plasticizer composition according to the second aspect of the present invention for achieving another object of the present invention comprises 50 to 100% by weight of the ester compound plasticizer according to the formula (1).
- Polyvinyl chloride resin composition according to a third aspect of the present invention for achieving another object of the present invention based on polyvinyl chloride resin, plasticizer composition according to the present invention 10 to 100 phr (parts per hundred resin) It provides a polyvinyl chloride resin composition comprising a.
- the polyvinyl chloride resin is manufactured using the ester plasticizer according to the present invention, an excellent product can be obtained in terms of plasticization efficiency, and in addition, physical properties such as hardness and tensile strength are improved.
- ester plasticizer compound and the polyvinyl chloride resin composition including the same according to the present invention will be described in detail.
- the ester plasticizer according to the present invention is a compound specified by Chemical Formula 1, wherein R 1 is a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, and R 2 is substituted or substituted with 6 to 10 carbon atoms.
- R 1 and R 2 are characterized by having asymmetric structures that are not identical to each other.
- R 1 is a substituted or unsubstituted alkyl group having 6 to 10 carbon atoms
- R 2 is a substituted or unsubstituted aryl group having 6 to 8 carbon atoms.
- R 1 and R 2 are the same as or different from each other, linear or branched alkyl group of 4 to 20 carbon atoms, alkenyl group of 4 to 20 carbon atoms, cycloalkyl group of 4 to 20 carbon atoms, or An aryl group of 6 to 10 may be included as a substituent.
- the ester plasticizer according to the present invention is prepared by, for example, reacting 1,4-butanediol with aromatic carboxylic acids and fatty acids.
- the molar ratio of aromatic carboxylic acid and fatty acid to 1,4-butanediol is 1: 0.7 to 0.2: 0.7 to 0.2, preferably 1: 0.4 to 0.25: 0.6 to 0.3, and this molar ratio is 1,4-butanediol It is based on the hydroxy group present in.
- Preferred catalysts are acid catalysts, for example sodium bisulfate. Examples of the catalyst that can be used include, for example, p-toluene sulfonic acid or sulfuric acid, and the catalyst may be used in an amount of 0.5 to 5 wt% based on the reaction mixture.
- Solvents that can be used are hexane, cyclohexane, toluene and xylene.
- the preferred temperature range for the reaction was found to be 100 to 160 ° C.
- the unreacted acid and acid catalyst are neutralized by the addition of an alkaline reagent such as aqueous sodium carbonate or calcium carbonate solution.
- an alkaline reagent such as aqueous sodium carbonate or calcium carbonate solution.
- the plasticizer composition according to the second aspect of the present invention includes 50 to 100% by weight of the ester compound plasticizer according to Chemical Formula 1.
- the plasticizer composition comprising the compound of Formula 1 may further include a compound of Formula 2 and / or Formula 3 in an amount of less than 50 wt% based on the total weight of the plasticizer composition.
- R 3 and R 4 are each independently a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms
- R 5 and R 6 are each independently a substituted or unsubstituted aryl group having 6 to 10 carbon atoms
- R 3 to R 6 are the same as or different from each other, a linear or branched alkyl group having 4 to 20 carbon atoms, alkenyl group having 4 to 20 carbon atoms, cycloalkyl group having 4 to 20 carbon atoms, or an aryl group having 6 to 10 carbon atoms It may be included as.
- the polyvinyl chloride resin composition according to the third aspect of the present invention may include the ester plasticizer composition according to the present invention in the range of 10 to 100 phr.
- the polyvinyl chloride resin is not limited to polyvinyl chloride, and chlorine-containing resins such as chlorinated polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, and vinyl chloride-vinyl acetate copolymers , Vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride- various vinyl ether copolymers, and the like.
- chlorine-containing resins such as chlorinated polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, and vinyl chloride-vinyl acetate copolymers , Vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer, vinyl chloride-isobutylene copolymer, vinyl
- Chlorine-containing resins and their mutual blends and also synthetic resins containing no chlorine-containing resins and chlorine, such as acrylonitrile-styrene copolymers, acrylonitrile-styrene-butadiene terpolymers, ethylene-vinyl acetate copolymers And blended products with polyester, etc., block copolymers, graft copolymers and the like.
- the plasticizer composition according to the present invention may be appropriately increased or decreased depending on the use of the resin composition. If it is added in excess of 100 phr, it is difficult to secure necessary mechanical properties and may be eluted.
- additives other than fillers and pigments may be generally included in the range of 0 to 30 phr with respect to the polyvinyl chloride resin.
- the insulation improver Various metal salts; Polyols; Epoxy compounds; Phenolic or sulfur antioxidants; Ultraviolet absorbers; Hindered amine light stabilizers; Inorganic stabilizers; Anti-fogging agents; Anti-misting agents; Stabilization aids; Well-known general additive components, such as an organotin compound, are mentioned.
- fillers and pigments may include up to about 200 phr of the polyvinyl chloride resin, which is not preferable because it affects density, hardness, or ductility.
- the fillers include calcium carbonate, silica, cray, glass beads, mica, sericite, glass flake, asbestos, wollastononaite, potassium titanate, PMF, Gypsum fiber, xonotlite, MOS, phosphate fiber, glass fiber, carbonate fiber, aramid fiber and the like.
- the polyvinyl chloride resin composition of the present invention containing an ester plasticizer according to the present invention includes building materials such as wall finishing materials, flooring materials, window frames, and wallpaper; Wire covering materials; Interior and exterior materials for automobiles; Agricultural materials such as houses and tunnels; Food packaging materials such as fish such as wraps and trays; Film forming agents such as underbody sealants, plastisols, paints, and inks; Synthetic leather, coated fabrics, hoses, pipes, sheets, baby toys, glove, and the like can be used in, but not limited to.
- the method for producing the polyvinyl chloride resin composition using the plasticizer is not particularly limited and may be prepared by methods well known in the art.
- the needle of the hardness tester (A Type) was completely lowered to one of the specimens, and the hardness value was read after 5 seconds, and the average value was taken after testing three places for each specimen. It is used as an index indicating plasticization efficiency.
- Brabender Tester was used to measure the maximum torque that appeared when mixing polyvinyl chloride resin and plasticizer.
- the unreacted organic acid and acid catalyst were neutralized with 10% by weight aqueous sodium carbonate solution, washed with water and dehydrated. Then, the adsorbent was added and filtered to finally form Benzoic acid 4-decanoyloxy-butyl ester as a main component (about 50%). Weight percent) to obtain a plasticizer composition.
- the press machine was used to preheat 1 minute, pressurized 1.5 minutes, and cooled for 2 minutes at 185 degrees to make a 2 mm sheet and to prepare various dumbbell-shaped specimens.
- a plasticizer and a polyvinyl chloride resin composition were prepared in the same manner as in Example 1, except that Octanoic acid was used instead of Decanoic acid as a raw material, and the experimental results are shown in Table 1 below.
- a plasticizer and a polyvinyl chloride resin composition were prepared in the same manner as in Example 1, except that Dodecanoic acid was used instead of Decanoic acid as a raw material, and the experimental results are shown in Table 1 below.
- a plasticizer and a polyvinyl chloride resin composition were prepared in the same manner as in Example 1 except for using 2-Ethyl hexanoic acid instead of Decanoic acid as a raw material, and the experimental results are shown in Table 1 below. It was.
- Specimens were prepared in the same manner as in Example 1, using the most widely used di-2-ethylhexylphthalate as the plasticizer. Tests were carried out in the same manner as in Example 1 with the prepared specimens and the results are summarized in Table 1 below.
- Example 1 Specimens were prepared in the same manner as in Example 1 by applying diisononylphthalate, which has been expanded in place of the di-2-ethylhexyl phthalate of Comparative Example 1, as a plasticizer. Tests were carried out in the same manner as in Example 1 with the prepared specimens and the results are summarized in Table 1 below.
- Specimens were prepared in the same manner as in Example 1 using trioctyl trimellitate as a plasticizer. Tests were carried out in the same manner as in Example 1 with the prepared specimens and the results are summarized in Table 1 below.
- Examples 1, 2 and 4 which are plasticizers of the present invention, are excellent in plasticizing efficiency compared to Comparative Examples 1, 2 and 3, which are the most common plasticizers, as well as other physical properties such as tensile strength, It can be seen that it is equal to or higher than elongation.
- Example 3, which is a similar series showed similar results as those of Comparative Example 1, which were highly related to the plasticization efficiency.
- the novel plasticizer of the present invention is excellent in plasticization efficiency, and thus can be expected to be more suitable for various molding according to the use and various applications.
Abstract
Description
Claims (8)
- 제1항에 있어서, 상기 R1은 탄소수 6 내지 10의 치환되거나 치환되지 않은 알킬기이고, 상기 R2는 탄소수 6 내지 8의 치환되거나 치환되지 않은 아릴기인 것을 특징으로 하는 에스테르계 가소제.
- 제1항에 있어서, 상기 R1 및 R2는 서로 같거나 다르게, 직쇄 또는 분지상의 탄소수 4 내지 20의 알킬기, 탄소수 4 내지 20의 알케닐기, 탄소수 4 내지 20의 시클로 알킬기, 또는 탄소수 6 내지 10의 아릴기를 치환기로서 포함하는 것을 특징으로 하는 에스테르계 가소제.
- 제1항에 따른 가소제를 50 내지 100중량%의 범위에서 포함하는 것을 특징으로 하는 에스테르계 가소제 조성물.
- 제5항에 있어서, 상기 R3 내지 R6는 서로 같거나 다르게, 직쇄 또는 분지상의 탄소수 4 내지 20의 알킬기, 탄소수 4 내지 20의 알케닐기, 탄소수 4 내지 20의 시클로 알킬기, 또는 탄소수 6 내지 10의 아릴기를 치환기로서 포함하는 것을 특징으로 하는 에스테르계 가소제.
- 폴리염화비닐수지에 대하여, 제4항 내지 제6항 중 어느 하나의 항에 따른 가소제 조성물을 10 내지 100phr의 범위로 포함하는 것을 특징으로 하는 폴리염화비닐 수지조성물.
- 제7항에 있어서, 상기 폴리염화비닐 수지 조성물은 폴리염화비닐 수지에 대하여, 충진제(Filler)와 안료를 제외한 첨가제가 30phr까지 더 포함되는 것을 특징으로 하는 폴리염화비닐 수지조성물.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CN2009801352931A CN102177131A (zh) | 2008-09-09 | 2009-08-28 | 增塑剂以及含有该增塑剂的聚氯乙烯树脂组合物 |
US13/063,031 US20110196081A1 (en) | 2008-09-09 | 2009-08-28 | Plasticizer and polyvinyl chloride resin composition containing same |
EP09813207.9A EP2343272A4 (en) | 2008-09-09 | 2009-08-28 | SOFT MAKER AND POLYVINYL CHLORIDE RESIN COMPOSITION THEREWITH |
JP2011525970A JP2012502021A (ja) | 2008-09-09 | 2009-08-28 | 可塑剤およびこれを含むポリ塩化ビニル樹脂組成物 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR10-2008-0088707 | 2008-09-09 | ||
KR1020080088707A KR20100029978A (ko) | 2008-09-09 | 2008-09-09 | 가소제 및 이를 포함한 폴리염화비닐 수지 조성물 |
Publications (2)
Publication Number | Publication Date |
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WO2010030085A2 true WO2010030085A2 (ko) | 2010-03-18 |
WO2010030085A3 WO2010030085A3 (ko) | 2010-06-17 |
Family
ID=42005601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/KR2009/004841 WO2010030085A2 (ko) | 2008-09-09 | 2009-08-28 | 가소제 및 이를 포함한 폴리염화비닐 수지 조성물 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20110196081A1 (ko) |
EP (1) | EP2343272A4 (ko) |
JP (1) | JP2012502021A (ko) |
KR (1) | KR20100029978A (ko) |
CN (1) | CN102177131A (ko) |
WO (1) | WO2010030085A2 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11124627B2 (en) | 2013-04-10 | 2021-09-21 | Performance Polyamides, Sas | Plasticizing composition |
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JP5305918B2 (ja) | 2005-11-22 | 2013-10-02 | サジティス・インコーポレイテッド | グリセロールレブリネートケタール類とその使用 |
CN102239156B (zh) * | 2008-09-25 | 2014-10-15 | 塞格提斯有限公司 | 缩酮酯衍生物 |
EP2445894B1 (en) | 2009-06-22 | 2016-03-02 | Segetis, Inc. | Ketal compounds and uses thereof |
US9539193B2 (en) | 2010-05-10 | 2017-01-10 | Gfbiochemicals Limited | Alkyl ketal esters as dispersants and slip agents for particulate solids, methods of manufacture, and uses thereof |
BR112013002991A2 (pt) | 2010-08-12 | 2016-08-16 | Segetis Inc | composições de revestimento de látex incluindo carboxiéster cetal coalescentes, métodos de fabricação e usos dos mesmos |
CA2803389C (en) | 2010-08-12 | 2016-10-11 | Segetis, Inc. | Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof |
EP2613760A2 (en) | 2010-09-07 | 2013-07-17 | Segetis, Inc. | Compositions for dyeing keratin fibers |
EP2630205A4 (en) | 2010-10-18 | 2015-01-21 | Segetis Inc | WATER-REDUCING COATING COMPOSITIONS COMPRISING CARBOXY ETHER KETALS, METHODS OF MAKING THE SAME, AND USES THEREOF |
KR101909434B1 (ko) * | 2010-11-29 | 2018-10-19 | 에스케이이노베이션 주식회사 | 수지 조성물용 가소제 및 이를 포함하는 수지 조성물 |
KR101282556B1 (ko) * | 2011-04-22 | 2013-07-04 | 주식회사 에네트 | 가소제 조성물 및 이의 제조방법 |
US9458414B2 (en) | 2012-09-21 | 2016-10-04 | Gfbiochemicals Limited | Cleaning, surfactant, and personal care compositions |
EP2925738B1 (en) | 2012-11-29 | 2018-01-10 | GFBiochemicals Limited | Carboxy ester ketals, methods of manufacture, and uses thereof |
KR102054881B1 (ko) * | 2013-10-24 | 2019-12-11 | 가부시키가이샤 아데카 | 에멀젼 수지용 성막 보조제 조성물 |
EP3081592B1 (en) * | 2013-12-10 | 2019-06-12 | Zeon Corporation | Vinyl chloride resin composition, vinyl chloride resin molded article, and laminate |
CA2941319A1 (en) * | 2014-03-18 | 2015-09-24 | Zeon Corporation | Vinyl chloride resin composition, vinyl chloride resin molded product, and laminate |
TW201619119A (zh) * | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及1,2-環己烷二羧酸酯的塑化劑組成物 |
TW201619120A (zh) * | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及對苯二甲酯之塑化劑組成物 |
US9856366B2 (en) * | 2015-04-10 | 2018-01-02 | Georgia-Pacific Chemicals Llc | Plastic compositions that include plasticizers containing an acylated phenolated fatty acid ester |
JP6817756B2 (ja) * | 2016-09-15 | 2021-01-20 | タイガースポリマー株式会社 | 耐放射線塩化ビニル樹脂組成物および耐放射線塩化ビニル樹脂組成物を含む可撓性ホースおよび可撓性チューブ |
JP6942221B2 (ja) * | 2016-09-21 | 2021-09-29 | タイガースポリマー株式会社 | 耐放射線塩化ビニル樹脂組成物および耐放射線塩化ビニル樹脂組成物を含む可撓性ホースおよび可撓性チューブ |
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2008
- 2008-09-09 KR KR1020080088707A patent/KR20100029978A/ko not_active Application Discontinuation
-
2009
- 2009-08-28 US US13/063,031 patent/US20110196081A1/en not_active Abandoned
- 2009-08-28 EP EP09813207.9A patent/EP2343272A4/en not_active Withdrawn
- 2009-08-28 CN CN2009801352931A patent/CN102177131A/zh active Pending
- 2009-08-28 JP JP2011525970A patent/JP2012502021A/ja active Pending
- 2009-08-28 WO PCT/KR2009/004841 patent/WO2010030085A2/ko active Application Filing
Non-Patent Citations (2)
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See also references of EP2343272A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11124627B2 (en) | 2013-04-10 | 2021-09-21 | Performance Polyamides, Sas | Plasticizing composition |
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KR20100029978A (ko) | 2010-03-18 |
JP2012502021A (ja) | 2012-01-26 |
CN102177131A (zh) | 2011-09-07 |
US20110196081A1 (en) | 2011-08-11 |
EP2343272A4 (en) | 2014-03-26 |
WO2010030085A3 (ko) | 2010-06-17 |
EP2343272A2 (en) | 2011-07-13 |
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