KR20150002693A - 시트르산의 테트라하이드로푸르푸릴 및/또는 알킬-치환 테트라하이드로푸르푸릴 에스테르를 함유하는 조성물 - Google Patents
시트르산의 테트라하이드로푸르푸릴 및/또는 알킬-치환 테트라하이드로푸르푸릴 에스테르를 함유하는 조성물 Download PDFInfo
- Publication number
- KR20150002693A KR20150002693A KR1020147029952A KR20147029952A KR20150002693A KR 20150002693 A KR20150002693 A KR 20150002693A KR 1020147029952 A KR1020147029952 A KR 1020147029952A KR 20147029952 A KR20147029952 A KR 20147029952A KR 20150002693 A KR20150002693 A KR 20150002693A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- composition
- citrate
- thf
- tetrahydrofurfuryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 172
- -1 tetrahydrofurfuryl Chemical group 0.000 title claims abstract description 138
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title abstract description 72
- 239000000463 material Substances 0.000 claims abstract description 99
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 31
- 125000002252 acyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 14
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- 239000004014 plasticizer Substances 0.000 abstract description 32
- 150000002148 esters Chemical class 0.000 abstract description 8
- OCTAFPWDRGGPDV-UHFFFAOYSA-N OC(=O)CC(O)(C(O)=O)CC(=O)OCC1CCCO1 Chemical compound OC(=O)CC(O)(C(O)=O)CC(=O)OCC1CCCO1 OCTAFPWDRGGPDV-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010128 melt processing Methods 0.000 abstract description 3
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- 230000032683 aging Effects 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
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- 239000000243 solution Substances 0.000 description 4
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical class CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
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- 239000003623 enhancer Substances 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
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- 239000012467 final product Substances 0.000 description 1
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- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
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- 239000012760 heat stabilizer Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000000329 molecular dynamics simulation Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
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- 239000010502 orange oil Substances 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- PCPUMGYALMOCHF-UHFFFAOYSA-N oxolan-3-ylmethanol Chemical compound OCC1CCOC1 PCPUMGYALMOCHF-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 229920001721 polyimide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- HDDLVZWGOPWKFW-UHFFFAOYSA-N trimethyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical class COC(=O)CC(O)(C(=O)OC)CC(=O)OC HDDLVZWGOPWKFW-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261618030P | 2012-03-30 | 2012-03-30 | |
| US61/618,030 | 2012-03-30 | ||
| PCT/US2013/031438 WO2013148255A1 (en) | 2012-03-30 | 2013-03-14 | Compositions containing tetrahydrofurfuryl and/or alkyl-substituted tetrahydrofurfuryl esters of citric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150002693A true KR20150002693A (ko) | 2015-01-07 |
Family
ID=48014346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147029952A Ceased KR20150002693A (ko) | 2012-03-30 | 2013-03-14 | 시트르산의 테트라하이드로푸르푸릴 및/또는 알킬-치환 테트라하이드로푸르푸릴 에스테르를 함유하는 조성물 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9670335B2 (https=) |
| EP (1) | EP2831065B1 (https=) |
| JP (1) | JP6138233B2 (https=) |
| KR (1) | KR20150002693A (https=) |
| CN (1) | CN104271570B (https=) |
| WO (1) | WO2013148255A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9828489B2 (en) | 2013-09-12 | 2017-11-28 | 3M Innovative Properties Company | Plasticized polymeric composition |
| WO2015065748A1 (en) | 2013-11-01 | 2015-05-07 | 3M Innovative Properties Company | Plasticized polymeric composition |
| US20160312003A1 (en) * | 2013-12-20 | 2016-10-27 | Proviron Holding N.V. | Succinate ester for use as plasticizer and biodegradable resins comprising this succinate ester |
| BE1021391B1 (nl) * | 2013-12-20 | 2015-11-13 | Proviron Holding | Estermengsel voor gebruik als weekmaker en kunststofsamenstellingen bevattende deze estermengsels |
| KR101913146B1 (ko) * | 2016-06-16 | 2018-11-01 | 주식회사 엘지화학 | 양친성 트리블록 고분자 |
| JP7113028B2 (ja) | 2017-06-28 | 2022-08-04 | ハンツマン ペトロケミカル エルエルシー | テトラヒドロフルフリルアルコール開始型ポリエーテルアミンおよびその使用 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2772776A (en) | 1954-01-07 | 1956-12-04 | United States Steel Corp | Apparatus and method for separating fines |
| GB805587A (en) | 1955-06-30 | 1958-12-10 | Goodyear Tire & Rubber | Plasticised linear aromatic polyester compositions |
| US4824893A (en) | 1984-06-11 | 1989-04-25 | Morflex Chemical Company, Inc. | Citrate esters and methods |
| US5055609A (en) | 1984-06-11 | 1991-10-08 | Morflex, Inc. | Method for producing citrates by esterification in the presence of organic titanates |
| US4870204A (en) | 1984-06-11 | 1989-09-26 | Morflex Chemical Company, Inc. | Method for preparing citrate esters |
| US4954649A (en) | 1984-06-11 | 1990-09-04 | Morflex Chemical Company, Inc. | Method for producing citrates |
| US4711922A (en) | 1985-05-17 | 1987-12-08 | Morflex Chemical Company, Inc. | Citrate esters and methods |
| US4892967A (en) | 1984-06-11 | 1990-01-09 | Morflex Chemical Company, Inc. | Citrate esters |
| US4931583A (en) | 1984-06-11 | 1990-06-05 | Morflex Chemical Compay, Inc. | Citrate esters |
| US4883905A (en) | 1984-06-11 | 1989-11-28 | Morflex Chemical Company, Inc. | Process for preparing citrates using organic titanates |
| US4789700A (en) | 1984-06-11 | 1988-12-06 | Morflex Chemical Company, Inc. | Citrate esters and method |
| US4710532A (en) | 1985-03-13 | 1987-12-01 | Morflex Chemical Company, Inc. | Medical article and method |
| US5026347A (en) | 1988-11-14 | 1991-06-25 | Baxter International Inc. | Plastic composition with anti-hemolytic effect |
| US4972036A (en) | 1989-08-28 | 1990-11-20 | Hi-Tek Polymers, Inc. | Thermosetting acrylic copolymers modified with citric esters |
| US5102926A (en) | 1990-10-30 | 1992-04-07 | Owens-Corning Fiberglas Corporation | Citrate ester compounds and processes for their preparation |
| CA2290092A1 (en) * | 1997-05-12 | 1998-11-19 | Eric F. V. Scriven | Processes for producing citrate esters |
| FR2772776B1 (fr) * | 1997-12-23 | 2002-03-29 | Atochem Elf Sa | Compositions antistatiques a base de polyamide |
| CA2322810A1 (en) | 1998-03-04 | 1999-09-10 | Ato B.V. | Bicyclooctane derivatives as plasticisers |
| JP2003082158A (ja) * | 2001-09-12 | 2003-03-19 | Arakawa Chem Ind Co Ltd | 樹脂用可塑剤および樹脂組成物 |
| CN100497452C (zh) | 2002-01-16 | 2009-06-10 | 伊士曼化工公司 | 用作聚合物的增塑剂的新型糖酯和多元醇酯、包含所述增塑剂的组合物和制品以及所述增塑剂的使用方法 |
| JP3421769B1 (ja) | 2002-04-02 | 2003-06-30 | 大八化学工業株式会社 | エステル化合物、生分解性脂肪族系ポリエステル樹脂用可塑剤及び生分解性樹脂組成物 |
| US20050272843A1 (en) | 2002-12-13 | 2005-12-08 | Mitsuaki Kobayashi | Aliphatic polyester resin composition |
| US20060094894A1 (en) | 2004-11-02 | 2006-05-04 | Day James F | Acylated esters |
| EP1683828B1 (en) | 2005-01-25 | 2011-11-16 | Jsp Corporation | Expandable polylactic acid resin particles |
| DE102008002168A1 (de) | 2008-06-03 | 2009-12-10 | Evonik Oxeno Gmbh | Zitronensäureestergemische und ihre Verwendung |
| JP5171674B2 (ja) | 2009-01-30 | 2013-03-27 | スリーエム イノベイティブ プロパティズ カンパニー | ポリ乳酸含有樹脂組成物、ポリ乳酸含有樹脂フィルム及びそれらの製造方法 |
| US8697787B2 (en) | 2009-09-30 | 2014-04-15 | Dow Global Technologies Llc | Flexible PVC compositions made with plasticizers derived from renewable sources |
| JP2013515822A (ja) * | 2009-12-28 | 2013-05-09 | スリーエム イノベイティブ プロパティズ カンパニー | 可塑化ポリラクチド |
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2013
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- 2013-03-14 JP JP2015503304A patent/JP6138233B2/ja not_active Expired - Fee Related
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- 2013-03-14 EP EP13713017.5A patent/EP2831065B1/en active Active
- 2013-03-14 KR KR1020147029952A patent/KR20150002693A/ko not_active Ceased
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|---|---|
| US20150033985A1 (en) | 2015-02-05 |
| EP2831065B1 (en) | 2018-08-08 |
| WO2013148255A1 (en) | 2013-10-03 |
| CN104271570B (zh) | 2017-08-18 |
| US9670335B2 (en) | 2017-06-06 |
| EP2831065A1 (en) | 2015-02-04 |
| JP6138233B2 (ja) | 2017-05-31 |
| CN104271570A (zh) | 2015-01-07 |
| JP2015518469A (ja) | 2015-07-02 |
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