DK2903964T3 - 14-HYDROXYEICOSANOIC ACID-BASED FATTY ACID AMID AS AN ORGANOGELATING AGENT - Google Patents
14-HYDROXYEICOSANOIC ACID-BASED FATTY ACID AMID AS AN ORGANOGELATING AGENT Download PDFInfo
- Publication number
- DK2903964T3 DK2903964T3 DK13782783.8T DK13782783T DK2903964T3 DK 2903964 T3 DK2903964 T3 DK 2903964T3 DK 13782783 T DK13782783 T DK 13782783T DK 2903964 T3 DK2903964 T3 DK 2903964T3
- Authority
- DK
- Denmark
- Prior art keywords
- acid
- amide
- diamide
- amine
- hsa
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 38
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 19
- 239000000194 fatty acid Substances 0.000 title claims description 19
- 229930195729 fatty acid Natural products 0.000 title claims description 19
- 150000004665 fatty acids Chemical class 0.000 title claims description 19
- 239000000203 mixture Substances 0.000 claims description 94
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 92
- 150000001408 amides Chemical class 0.000 claims description 55
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 42
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 30
- -1 aliphatic amines Chemical class 0.000 claims description 18
- 238000000518 rheometry Methods 0.000 claims description 18
- 239000000654 additive Substances 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- 239000011230 binding agent Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
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- 230000000996 additive effect Effects 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
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- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 4
- 125000004427 diamine group Chemical group 0.000 claims description 4
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- 125000003368 amide group Chemical group 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
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- 150000004982 aromatic amines Chemical class 0.000 claims description 2
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- 238000005266 casting Methods 0.000 claims description 2
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000565 sealant Substances 0.000 claims 2
- 229920006397 acrylic thermoplastic Polymers 0.000 claims 1
- 125000004420 diamide group Chemical group 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims 1
- MLXZFCNGEWQIAB-UHFFFAOYSA-N 14-hydroxyicosanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCCCC(O)=O MLXZFCNGEWQIAB-UHFFFAOYSA-N 0.000 description 48
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- 241000390166 Physaria Species 0.000 description 14
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
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- 238000002360 preparation method Methods 0.000 description 12
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- 150000001470 diamides Chemical class 0.000 description 11
- 230000004913 activation Effects 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000004359 castor oil Substances 0.000 description 9
- 235000019438 castor oil Nutrition 0.000 description 9
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 8
- OONXYOAWMIVMCI-UHFFFAOYSA-N D-Lesquerolinsaeure Natural products CCCCCCC(O)CC=CCCCCCCCCCC(O)=O OONXYOAWMIVMCI-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
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- OONXYOAWMIVMCI-KWRJMZDGSA-N lesquerolic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCCCC(O)=O OONXYOAWMIVMCI-KWRJMZDGSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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- 238000012360 testing method Methods 0.000 description 5
- PAZZVPKITDJCPV-UHFFFAOYSA-N 10-hydroxyoctadecanoic acid Chemical class CCCCCCCCC(O)CCCCCCCCC(O)=O PAZZVPKITDJCPV-UHFFFAOYSA-N 0.000 description 4
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000006140 methanolysis reaction Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
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- 238000007127 saponification reaction Methods 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- RKHXDCVAPIMDMG-UHFFFAOYSA-N 9-Hydroxyoctadecanoic acid Natural products CCCCCCCCCC(O)CCCCCCCC(O)=O RKHXDCVAPIMDMG-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 238000000622 liquid--liquid extraction Methods 0.000 description 3
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- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- GWEIHUNYMRRZJJ-UHFFFAOYSA-N Auricolic acid Natural products CCC=CCCC(O)CC=CCCCCCCCCCC(O)=O GWEIHUNYMRRZJJ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 230000008569 process Effects 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
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- OONXYOAWMIVMCI-SDNWHVSQSA-N (e)-14-hydroxyicos-11-enoic acid Chemical compound CCCCCCC(O)C\C=C\CCCCCCCCCC(O)=O OONXYOAWMIVMCI-SDNWHVSQSA-N 0.000 description 1
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- OKIDIWHWTIMACU-MNEPGTOVSA-N 12R-HODE Chemical compound CC\C=C/CC[C@@H](O)C\C=C/CCCCCCCC(O)=O OKIDIWHWTIMACU-MNEPGTOVSA-N 0.000 description 1
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- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1259491A FR2996553B1 (fr) | 2012-10-05 | 2012-10-05 | Amide d'acide gras a base d'acide 14-hydroxy-eicosanoique, comme organogelateur |
| PCT/FR2013/052346 WO2014053774A1 (fr) | 2012-10-05 | 2013-10-02 | Amide d'acide gras a base d'acide 14-hydroxy-eicosanoique, comme organogelateur. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2903964T3 true DK2903964T3 (en) | 2018-11-19 |
Family
ID=47598880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13782783.8T DK2903964T3 (en) | 2012-10-05 | 2013-10-02 | 14-HYDROXYEICOSANOIC ACID-BASED FATTY ACID AMID AS AN ORGANOGELATING AGENT |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20150274644A1 (enExample) |
| EP (1) | EP2903964B1 (enExample) |
| JP (1) | JP6118909B2 (enExample) |
| KR (1) | KR101782233B1 (enExample) |
| CN (1) | CN104718186B (enExample) |
| BR (1) | BR112015007238A2 (enExample) |
| DK (1) | DK2903964T3 (enExample) |
| FR (1) | FR2996553B1 (enExample) |
| IN (1) | IN2015KN00680A (enExample) |
| WO (1) | WO2014053774A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4223841A3 (en) | 2015-07-31 | 2023-09-13 | Elementis Specialties, Inc. | Polyamide compositions for sealants and high solids paints |
| FR3043087B1 (fr) * | 2015-11-02 | 2018-04-27 | Arkema France | Composition d'additif diamide gras pre-concentree et pre-activee dans un diluant reactif |
| MX2018010183A (es) * | 2016-02-26 | 2019-05-02 | Evonik Degussa Gmbh | Amidas de poliaminas alifaticas y acido 12-hidroxioctadecanoico y composiciones espesantes estables a la lipasa. |
| CA3015518C (en) * | 2016-02-26 | 2021-04-06 | The Procter & Gamble Company | Thickened or structured liquid detergent compositions |
| CN110248992B (zh) * | 2017-02-10 | 2021-05-28 | 毕克化学有限公司 | 粉末颗粒状二酰胺-聚烯烃蜡混合物 |
| FR3073843A1 (fr) * | 2017-11-21 | 2019-05-24 | Arkema France | Additifs de rheologie a base de di- ou tri-amides et de leurs melanges |
| FR3087779B1 (fr) * | 2018-10-26 | 2021-10-08 | Arkema France | Additif de rheologie a base de diamine biosourcee |
| FR3094367B1 (fr) | 2019-03-29 | 2023-03-03 | Arkema France | Additifs de rhéologie à base de di- ou tri-amides hydroxyles et de leurs mélanges |
| EP4289886A1 (en) | 2022-06-10 | 2023-12-13 | Arkema France | Continuous or semi-continuous process for producing a pre-activated organogelator paste |
| CN116874774A (zh) * | 2023-06-16 | 2023-10-13 | 浙江丰虹新材料股份有限公司 | 一种用于密封胶或胶黏剂用高温活化蜡粉的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128436A (en) * | 1974-05-29 | 1978-12-05 | Coats Brothers & Company Ltd. | Rheological agents |
| GB1461355A (en) * | 1974-05-29 | 1977-01-13 | Coates Bros Co Ltd | Rheological agents |
| US20090223409A1 (en) * | 2008-03-07 | 2009-09-10 | Xerox Corporation | Compounds suitable for use in inks and inks having such compounds |
| WO2010100939A1 (ja) * | 2009-03-06 | 2010-09-10 | 株式会社コーセー | 油ゲル化剤、該油ゲル化剤を含有する油ゲル組成物及び該油ゲル組成物を含有する皮膚外用剤又は化粧料 |
| US9109150B2 (en) * | 2010-03-08 | 2015-08-18 | Georgetown University | Fast recovery of thixotropy by organogels with low molecular weight gelators |
| US20120129735A1 (en) * | 2010-11-19 | 2012-05-24 | Elementis Specialties, Inc. | Non-aqueous drilling additive useful to produce a flat temperature-rheology profile |
-
2012
- 2012-10-05 FR FR1259491A patent/FR2996553B1/fr active Active
-
2013
- 2013-10-02 CN CN201380052010.3A patent/CN104718186B/zh not_active Expired - Fee Related
- 2013-10-02 JP JP2015535090A patent/JP6118909B2/ja active Active
- 2013-10-02 IN IN680KON2015 patent/IN2015KN00680A/en unknown
- 2013-10-02 BR BR112015007238A patent/BR112015007238A2/pt not_active IP Right Cessation
- 2013-10-02 DK DK13782783.8T patent/DK2903964T3/en active
- 2013-10-02 KR KR1020157011762A patent/KR101782233B1/ko active Active
- 2013-10-02 US US14/432,233 patent/US20150274644A1/en not_active Abandoned
- 2013-10-02 EP EP13782783.8A patent/EP2903964B1/fr active Active
- 2013-10-02 WO PCT/FR2013/052346 patent/WO2014053774A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20150274644A1 (en) | 2015-10-01 |
| KR101782233B1 (ko) | 2017-09-26 |
| FR2996553A1 (fr) | 2014-04-11 |
| EP2903964A1 (fr) | 2015-08-12 |
| CN104718186B (zh) | 2017-10-13 |
| EP2903964B1 (fr) | 2018-08-08 |
| CN104718186A (zh) | 2015-06-17 |
| JP6118909B2 (ja) | 2017-04-19 |
| KR20150065188A (ko) | 2015-06-12 |
| BR112015007238A2 (pt) | 2017-07-04 |
| JP2015535846A (ja) | 2015-12-17 |
| FR2996553B1 (fr) | 2015-09-04 |
| WO2014053774A1 (fr) | 2014-04-10 |
| IN2015KN00680A (enExample) | 2015-07-17 |
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