WO1997031950A1 - Carboxymethyl cellulose ethers having, as substituents, long chain groups - Google Patents
Carboxymethyl cellulose ethers having, as substituents, long chain groups Download PDFInfo
- Publication number
- WO1997031950A1 WO1997031950A1 PCT/EP1997/000949 EP9700949W WO9731950A1 WO 1997031950 A1 WO1997031950 A1 WO 1997031950A1 EP 9700949 W EP9700949 W EP 9700949W WO 9731950 A1 WO9731950 A1 WO 9731950A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carboxymethyl cellulose
- group
- alkyl
- branched
- linear
- Prior art date
Links
- 229920002134 Carboxymethyl cellulose Polymers 0.000 title claims abstract description 40
- 239000001768 carboxy methyl cellulose Substances 0.000 title claims abstract description 39
- 235000010948 carboxy methyl cellulose Nutrition 0.000 title claims abstract description 39
- 239000008112 carboxymethyl-cellulose Substances 0.000 title claims abstract description 39
- 150000002170 ethers Chemical class 0.000 title claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 title claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000006467 substitution reaction Methods 0.000 claims abstract description 9
- 239000000654 additive Substances 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 6
- 239000002537 cosmetic Substances 0.000 claims abstract description 4
- 239000003973 paint Substances 0.000 claims abstract description 4
- 230000008719 thickening Effects 0.000 claims abstract description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- -1 polyoxyethylene Polymers 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 5
- 239000003444 phase transfer catalyst Substances 0.000 claims description 5
- 150000001875 compounds Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003556 assay Methods 0.000 description 7
- 230000004907 flux Effects 0.000 description 7
- 230000029936 alkylation Effects 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 5
- QYOXLKAKUAASNA-UHFFFAOYSA-N 1-bromodocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCBr QYOXLKAKUAASNA-UHFFFAOYSA-N 0.000 description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical group [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 3
- 229940083575 sodium dodecyl sulfate Drugs 0.000 description 3
- FPNCDGKCAWKFEK-UHFFFAOYSA-N 1-methylsulfonyldocosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCS(C)(=O)=O FPNCDGKCAWKFEK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- ZNSKJUSTKPCZPG-UHFFFAOYSA-N 2-(dodecoxymethylidene)oxirane Chemical compound C(CCCCCCCCCCC)OC=C1OC1 ZNSKJUSTKPCZPG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical class C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005373 porous glass Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/731—Cellulose; Quaternized cellulose derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/193—Mixed ethers, i.e. ethers with two or more different etherifying groups
Definitions
- carboxymethyl cellulose having a degree of substitution in carboxymethyl groups (D. S.) ranging from 0.5 to 1.2, determined according to the ASTM D1439 method, are preferred.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI96A000375 | 1996-02-28 | ||
| IT96MI000375A IT1282703B1 (it) | 1996-02-28 | 1996-02-28 | Eteri della carbossimetilcellulosa aventi,come sostituenti,gruppi a catena lunga |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997031950A1 true WO1997031950A1 (en) | 1997-09-04 |
| WO1997031950B1 WO1997031950B1 (en) | 1998-02-19 |
Family
ID=11373424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1997/000949 WO1997031950A1 (en) | 1996-02-28 | 1997-02-27 | Carboxymethyl cellulose ethers having, as substituents, long chain groups |
Country Status (2)
| Country | Link |
|---|---|
| IT (1) | IT1282703B1 (enrdf_load_stackoverflow) |
| WO (1) | WO1997031950A1 (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000035957A1 (en) * | 1998-12-11 | 2000-06-22 | Akzo Nobel N.V. | Anionic cellulose ethers having temperature-dependent associative properties |
| US6384011B1 (en) | 1997-09-15 | 2002-05-07 | The Procter & Gamble Company | Laundry detergent compositions with cellulosic based polymers to provide appearance and integrity benefits to fabrics laundered therewith |
| JP2002522569A (ja) * | 1998-08-06 | 2002-07-23 | アクゾ・ノーベル・ナムローゼ・フエンノートシャップ | 増粘特性が改良された非イオン性セルロースエーテル |
| US6669863B1 (en) | 1998-12-11 | 2003-12-30 | Akzo Nobel N.V. | Anionic cellulose ethers having temperature-dependent associative properties |
| EP1369102A4 (en) * | 2001-03-16 | 2005-11-09 | Kao Corp | WATER OIL EMULSION AND PROCESS FOR PREPARING THE SAME |
| EP1598044A1 (en) * | 2004-04-27 | 2005-11-23 | Kao Corporation | Oil-in-water emulsion and process for producing the same |
| USRE39557E1 (en) * | 1997-09-15 | 2007-04-10 | The Procter & Gamble Company | Laundry detergent compositions with cellulosic based polymers to provide appearance and integrity benefits to fabrics laundered therewith |
| FR2952375A1 (fr) * | 2009-11-10 | 2011-05-13 | Adocia | Polysaccharides comportant des groupes fonctionnels carboxyles substitues par esterification par un derive d'alcool hydrophobe |
| CN114621736A (zh) * | 2021-12-08 | 2022-06-14 | 中国石油天然气集团有限公司 | 一种环境友好型钻井液封堵剂、钻井液以及制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD140049A1 (de) * | 1978-11-28 | 1980-02-06 | Fritz Loth | Verfahren zur herstellung von cellulosemischaethern |
| EP0136722A2 (en) * | 1983-10-06 | 1985-04-10 | Kohjin Co., Ltd. | Process for preparing carboxymethyl ethyl cellulose suitable for enteric coating |
-
1996
- 1996-02-28 IT IT96MI000375A patent/IT1282703B1/it active IP Right Grant
-
1997
- 1997-02-27 WO PCT/EP1997/000949 patent/WO1997031950A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD140049A1 (de) * | 1978-11-28 | 1980-02-06 | Fritz Loth | Verfahren zur herstellung von cellulosemischaethern |
| EP0136722A2 (en) * | 1983-10-06 | 1985-04-10 | Kohjin Co., Ltd. | Process for preparing carboxymethyl ethyl cellulose suitable for enteric coating |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE39557E1 (en) * | 1997-09-15 | 2007-04-10 | The Procter & Gamble Company | Laundry detergent compositions with cellulosic based polymers to provide appearance and integrity benefits to fabrics laundered therewith |
| US6384011B1 (en) | 1997-09-15 | 2002-05-07 | The Procter & Gamble Company | Laundry detergent compositions with cellulosic based polymers to provide appearance and integrity benefits to fabrics laundered therewith |
| JP2002522569A (ja) * | 1998-08-06 | 2002-07-23 | アクゾ・ノーベル・ナムローゼ・フエンノートシャップ | 増粘特性が改良された非イオン性セルロースエーテル |
| US6669863B1 (en) | 1998-12-11 | 2003-12-30 | Akzo Nobel N.V. | Anionic cellulose ethers having temperature-dependent associative properties |
| WO2000035957A1 (en) * | 1998-12-11 | 2000-06-22 | Akzo Nobel N.V. | Anionic cellulose ethers having temperature-dependent associative properties |
| EP1369102A4 (en) * | 2001-03-16 | 2005-11-09 | Kao Corp | WATER OIL EMULSION AND PROCESS FOR PREPARING THE SAME |
| US7517534B2 (en) | 2001-03-16 | 2009-04-14 | Kao Corporation | Oil-in-water emulsions and process for producing the same |
| EP1598044A1 (en) * | 2004-04-27 | 2005-11-23 | Kao Corporation | Oil-in-water emulsion and process for producing the same |
| US7511002B2 (en) | 2004-04-27 | 2009-03-31 | Kao Corporation | Oil-in-water emulsion and process for producing the same |
| FR2952375A1 (fr) * | 2009-11-10 | 2011-05-13 | Adocia | Polysaccharides comportant des groupes fonctionnels carboxyles substitues par esterification par un derive d'alcool hydrophobe |
| WO2011135401A1 (fr) * | 2009-11-10 | 2011-11-03 | Adocia | Polysaccharides comportant des groupes fonctionnels carboxyles substitues par esterification par un alcool hydrophobe |
| CN114621736A (zh) * | 2021-12-08 | 2022-06-14 | 中国石油天然气集团有限公司 | 一种环境友好型钻井液封堵剂、钻井液以及制备方法 |
| CN114621736B (zh) * | 2021-12-08 | 2024-03-19 | 中国石油天然气集团有限公司 | 一种环境友好型钻井液封堵剂、钻井液以及制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1282703B1 (it) | 1998-03-31 |
| ITMI960375A1 (it) | 1997-08-28 |
| ITMI960375A0 (enrdf_load_stackoverflow) | 1996-02-28 |
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