KR102786287B1 - 올리고에스테르 및 이의 조성물 - Google Patents
올리고에스테르 및 이의 조성물 Download PDFInfo
- Publication number
- KR102786287B1 KR102786287B1 KR1020187022193A KR20187022193A KR102786287B1 KR 102786287 B1 KR102786287 B1 KR 102786287B1 KR 1020187022193 A KR1020187022193 A KR 1020187022193A KR 20187022193 A KR20187022193 A KR 20187022193A KR 102786287 B1 KR102786287 B1 KR 102786287B1
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- KR
- South Korea
- Prior art keywords
- acid
- oligoester
- rosin
- oligoester composition
- acids
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 450
- 229920002601 oligoester Polymers 0.000 title claims abstract description 366
- 239000002253 acid Substances 0.000 claims abstract description 168
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims abstract description 152
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims abstract description 152
- 238000000034 method Methods 0.000 claims abstract description 138
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- 238000005886 esterification reaction Methods 0.000 claims abstract description 55
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- 239000011541 reaction mixture Substances 0.000 claims abstract description 23
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 211
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- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
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- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920000223 polyglycerol Polymers 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 5
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 claims description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 5
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 claims description 5
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- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 claims description 4
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims description 4
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 4
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 3
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- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 3
- GWZCCUDJHOGOSO-UHFFFAOYSA-N diphenic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1C(O)=O GWZCCUDJHOGOSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000832 lactitol Substances 0.000 claims description 3
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- 150000007970 thio esters Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/46—Polyesters chemically modified by esterification
- C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
-
- 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
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- 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
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/06—Copolymers with styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562273760P | 2015-12-31 | 2015-12-31 | |
| US62/273,760 | 2015-12-31 | ||
| PCT/US2016/069594 WO2017117576A1 (en) | 2015-12-31 | 2016-12-30 | Oligoesters and compositions thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20180103941A KR20180103941A (ko) | 2018-09-19 |
| KR102786287B1 true KR102786287B1 (ko) | 2025-03-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020187022193A Active KR102786287B1 (ko) | 2015-12-31 | 2016-12-30 | 올리고에스테르 및 이의 조성물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10435586B2 (enExample) |
| EP (1) | EP3397709B1 (enExample) |
| JP (1) | JP6942723B2 (enExample) |
| KR (1) | KR102786287B1 (enExample) |
| CN (1) | CN108699395B (enExample) |
| TW (1) | TWI751132B (enExample) |
| WO (1) | WO2017117576A1 (enExample) |
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| US10927234B2 (en) | 2018-01-17 | 2021-02-23 | Kraton Polymers U.S. Llc | PVC plasticizers and methods for making thereof |
| JP7042661B2 (ja) * | 2018-03-20 | 2022-03-28 | 株式会社きもと | 機能性部材 |
| EP3847213A1 (en) * | 2018-09-03 | 2021-07-14 | Sika Technology AG | Thermally expandable rubber composition |
| CN110184034A (zh) * | 2019-05-21 | 2019-08-30 | 浙江理工大学 | 一种双酯型耐高温相变储能材料及其制备方法 |
| CN110205072B (zh) * | 2019-06-14 | 2021-05-04 | 上海天洋热熔粘接材料股份有限公司 | 基于2,5-呋喃二甲酸的共聚酯热熔胶及其制备方法 |
| PL3986972T3 (pl) | 2019-06-18 | 2025-01-13 | Avery Dennison Corporation | Kleje przylepcowe na bazie kauczuku butylowego |
| US11634562B2 (en) * | 2019-09-20 | 2023-04-25 | Kraton Corporation | Tire composition and method for making thereof |
| CN110655644B (zh) * | 2019-10-12 | 2021-09-07 | 黄山市向荣新材料有限公司 | 60/40低光型粉末涂料用聚酯树脂及其三釜联用制备方法 |
| CN110684183A (zh) * | 2019-11-08 | 2020-01-14 | 商丘市博大化工有限公司 | 含金刚烷结构的聚酯多元醇树脂及制备方法 |
| ES2992290T3 (es) | 2019-12-20 | 2024-12-11 | Harima Chemicals Inc | Composición de resina para tintas acuosas |
| GB202000685D0 (en) * | 2020-01-16 | 2020-03-04 | Croda Int Plc | Film & Seed coating composition |
| JP6914606B1 (ja) * | 2020-05-26 | 2021-08-04 | ハリマ化成株式会社 | 活性エネルギー線硬化型インキ用樹脂、活性エネルギー線硬化型インキ用組成物および活性エネルギー線硬化型インキ |
| US11466176B2 (en) | 2020-08-14 | 2022-10-11 | Bmic Llc | Non-asphaltic coatings, non-asphaltic roofing materials, and methods of making the same |
| CN111876229A (zh) * | 2020-08-18 | 2020-11-03 | 上海金兆节能科技有限公司 | 抗磨润滑剂组合物及其制备方法及组合物制备的微量润滑剂 |
| EP4092085B1 (en) * | 2021-05-11 | 2025-01-01 | Kraton Polymers Research B.V. | Associative rheology modifier composition and methods for making thereof |
| US20220363962A1 (en) * | 2021-05-13 | 2022-11-17 | Ingevity South Carolina, Llc | Uv or eb curable multifunctional tall oil (meth)acrylates |
| CN114381236B (zh) * | 2021-12-15 | 2024-02-02 | 杭州鲁尔新材料科技有限公司 | 一种易于灌装的高粘度相变材料 |
| EP4522695A1 (de) | 2022-05-12 | 2025-03-19 | Henkel AG & Co. KGaA | Haftklebstoff enthaltend flüssigharz umfassend eine oligoesterzusammensetzung |
| CN116162411B (zh) * | 2022-09-08 | 2025-09-05 | 吉安新茂林化有限公司 | 一种松香树脂的制备方法 |
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| JP7521660B1 (ja) | 2023-07-12 | 2024-07-24 | ａｒｔｉｅｎｃｅ株式会社 | 粘着剤および粘着シート |
| WO2025094609A1 (ja) * | 2023-10-30 | 2025-05-08 | ハリマ化成株式会社 | ゴム用添加剤、ゴム組成物およびタイヤ |
| WO2025239067A1 (ja) * | 2024-05-14 | 2025-11-20 | 綜研化学株式会社 | 粘着剤組成物および粘着シート |
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| JP5519996B2 (ja) * | 2009-10-20 | 2014-06-11 | 日東電工株式会社 | 表面保護用粘着シート |
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| FR3009304B1 (fr) | 2013-08-05 | 2016-09-30 | A Et A Mader | Resine alkyde biosourcee et procede de fabrication d'unte telle resine alkyde |
| US10167365B2 (en) | 2013-10-11 | 2019-01-01 | Dsm Ip Assets B.V. | Polymer and composition |
| IN2013CH04900A (enExample) | 2013-10-31 | 2015-05-08 | Empire Technology Dev Llc |
-
2016
- 2016-12-30 JP JP2018553851A patent/JP6942723B2/ja active Active
- 2016-12-30 EP EP16882785.5A patent/EP3397709B1/en active Active
- 2016-12-30 KR KR1020187022193A patent/KR102786287B1/ko active Active
- 2016-12-30 US US15/396,258 patent/US10435586B2/en active Active
- 2016-12-30 CN CN201680080118.7A patent/CN108699395B/zh active Active
- 2016-12-30 WO PCT/US2016/069594 patent/WO2017117576A1/en not_active Ceased
-
2017
- 2017-01-03 TW TW106100049A patent/TWI751132B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3397709C0 (en) | 2023-10-11 |
| US20170190935A1 (en) | 2017-07-06 |
| WO2017117576A1 (en) | 2017-07-06 |
| KR20180103941A (ko) | 2018-09-19 |
| CN108699395A (zh) | 2018-10-23 |
| CN108699395B (zh) | 2022-03-01 |
| EP3397709A4 (en) | 2019-08-07 |
| TWI751132B (zh) | 2022-01-01 |
| JP6942723B2 (ja) | 2021-09-29 |
| TW201739856A (zh) | 2017-11-16 |
| EP3397709B1 (en) | 2023-10-11 |
| US10435586B2 (en) | 2019-10-08 |
| JP2019501276A (ja) | 2019-01-17 |
| EP3397709A1 (en) | 2018-11-07 |
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