CN101687771B - 用于制备具有一个或多个季铵基团的丙烯酸系单体及其聚合物的方法 - Google Patents
用于制备具有一个或多个季铵基团的丙烯酸系单体及其聚合物的方法 Download PDFInfo
- Publication number
- CN101687771B CN101687771B CN200880009512.7A CN200880009512A CN101687771B CN 101687771 B CN101687771 B CN 101687771B CN 200880009512 A CN200880009512 A CN 200880009512A CN 101687771 B CN101687771 B CN 101687771B
- Authority
- CN
- China
- Prior art keywords
- monomer
- aqueous medium
- group
- reaction
- quaternary ammonium
- 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.)
- Expired - Fee Related
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 19
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 16
- 229920000642 polymer Polymers 0.000 title claims description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 239000012736 aqueous medium Substances 0.000 claims abstract description 32
- 239000000376 reactant Substances 0.000 claims abstract description 23
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- 238000012544 monitoring process Methods 0.000 claims abstract description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- -1 3-chloro-2-hydroxypropyl Chemical group 0.000 description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 description 2
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000012035 limiting reagent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 0 **(*)(**1ON1)*=C Chemical compound **(*)(**1ON1)*=C 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UNYOJUYSNFGNDV-UHFFFAOYSA-M magnesium monohydroxide Chemical compound [Mg]O UNYOJUYSNFGNDV-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/12—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/62—Quaternary ammonium compounds
- C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
- C08F220/606—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen and containing other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91970507P | 2007-03-23 | 2007-03-23 | |
| US60/919,705 | 2007-03-23 | ||
| PCT/US2008/003589 WO2008118315A1 (en) | 2007-03-23 | 2008-03-19 | Process for making an acrylic monomer having one or more quaternary ammonium groups and its polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101687771A CN101687771A (zh) | 2010-03-31 |
| CN101687771B true CN101687771B (zh) | 2014-06-18 |
Family
ID=39775407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880009512.7A Expired - Fee Related CN101687771B (zh) | 2007-03-23 | 2008-03-19 | 用于制备具有一个或多个季铵基团的丙烯酸系单体及其聚合物的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7858722B2 (enExample) |
| EP (1) | EP2139849A4 (enExample) |
| JP (1) | JP5185297B2 (enExample) |
| KR (1) | KR101572596B1 (enExample) |
| CN (1) | CN101687771B (enExample) |
| BR (1) | BRPI0809312A2 (enExample) |
| CA (1) | CA2681763A1 (enExample) |
| RU (1) | RU2471773C2 (enExample) |
| WO (1) | WO2008118315A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8541523B2 (en) | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| CN102580607B (zh) * | 2011-12-30 | 2014-02-19 | 武汉理工大学 | 双季铵盐慢裂快凝沥青乳化剂的合成工艺 |
| CN103554526B (zh) * | 2013-10-18 | 2015-03-04 | 辽宁石油化工大学 | 一种引入双季铵阳离子分子的阴离子交换膜及其制备方法 |
| WO2018232115A1 (en) | 2017-06-15 | 2018-12-20 | Ecolab Usa Inc. | Polymer for pitch and stickies deposition control in papermaking |
| CN107619660B (zh) * | 2017-11-02 | 2020-04-14 | 中国石油化工股份有限公司 | 胶凝酸稠化剂及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495367A (en) * | 1982-07-06 | 1985-01-22 | Celanese Corporation | High charge density, cationic methacrylamide based monomers and their _polymers |
| US4973637A (en) * | 1989-02-23 | 1990-11-27 | Hi-Tek Polymers, Inc. | Polymers made from quaternary ammonium acrylic monomers |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2856384C3 (de) * | 1978-12-27 | 1981-11-19 | Chemische Fabrik Stockhausen & Cie, 4150 Krefeld | Quartäre Ammoniumgruppen enthaltende Acrylyl- bzw. Methacrylylharnstoffe und Verfahren zu ihrer Herstellung |
| US4387017A (en) * | 1981-12-02 | 1983-06-07 | Texaco Inc. | Demulsification of bitumen emulsions using polymers of diquaternary ammonium monomers containing hydroxyl groups |
| CA1235140A (en) * | 1982-07-06 | 1988-04-12 | Laurence G. Dammann | High charge density, cationic methacrylamide based monomers and their polymers |
| CA1235141A (en) * | 1984-03-28 | 1988-04-12 | Laurence G. Dammann | High charge density, cationic methacrylamide based monomers and their polymers |
| JPH0768678B2 (ja) * | 1985-10-04 | 1995-07-26 | 日本ピー・エム・シー株式会社 | 製紙用添加剤 |
| RU2061679C1 (ru) * | 1993-01-19 | 1996-06-10 | Нижегородский политехнический институт | Соли n-[1,1-r,r-3-диметиламинопропил(поли-1,1-r,r,-7-оксо-4,4-диметил-4,8-диазаоктаметилен)]пропенамидов и способ их получения |
| FR2796392B1 (fr) * | 1999-07-15 | 2003-09-19 | Rhodia Chimie Sa | Composition nettoyante comprenant un polymere hydrosoluble ou hydrodispersable |
| US6596261B1 (en) | 2000-01-25 | 2003-07-22 | Aeropharm Technology Incorporated | Method of administering a medicinal aerosol formulation |
| WO2003101410A1 (en) | 2002-06-04 | 2003-12-11 | The Procter & Gamble Company | Conditioning shampoo composition containing select cationic conditioning polymers |
| PL374040A1 (en) | 2002-06-04 | 2005-09-19 | Rhodia Inc. | Monomer compound comprising several cationic groups, process for making the same, and polymers comprising units deriving therefrom |
| US7064232B2 (en) | 2003-12-08 | 2006-06-20 | Rhodia Inc. | Hydrophobic modified diquaternary monomers and polymers as thickening agents of acidic aqueous compositions |
-
2008
- 2008-03-19 EP EP08726971A patent/EP2139849A4/en not_active Withdrawn
- 2008-03-19 JP JP2009554559A patent/JP5185297B2/ja not_active Expired - Fee Related
- 2008-03-19 US US12/077,326 patent/US7858722B2/en not_active Expired - Fee Related
- 2008-03-19 BR BRPI0809312-1A2A patent/BRPI0809312A2/pt not_active Application Discontinuation
- 2008-03-19 CA CA002681763A patent/CA2681763A1/en not_active Abandoned
- 2008-03-19 WO PCT/US2008/003589 patent/WO2008118315A1/en not_active Ceased
- 2008-03-19 CN CN200880009512.7A patent/CN101687771B/zh not_active Expired - Fee Related
- 2008-03-19 RU RU2009139076/04A patent/RU2471773C2/ru not_active IP Right Cessation
- 2008-03-19 KR KR1020097019448A patent/KR101572596B1/ko not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4495367A (en) * | 1982-07-06 | 1985-01-22 | Celanese Corporation | High charge density, cationic methacrylamide based monomers and their _polymers |
| US4973637A (en) * | 1989-02-23 | 1990-11-27 | Hi-Tek Polymers, Inc. | Polymers made from quaternary ammonium acrylic monomers |
Non-Patent Citations (1)
| Title |
|---|
| Robert Voeffray, et al..193. L-Carnitine. Novel Synthesis and Determination of the Optical Purity.《HELVETICA CHIMICA ACTA》.1987,第70卷第2058-2064页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010522167A (ja) | 2010-07-01 |
| US20080234432A1 (en) | 2008-09-25 |
| CA2681763A1 (en) | 2008-10-02 |
| US7858722B2 (en) | 2010-12-28 |
| KR20100014452A (ko) | 2010-02-10 |
| CN101687771A (zh) | 2010-03-31 |
| EP2139849A1 (en) | 2010-01-06 |
| JP5185297B2 (ja) | 2013-04-17 |
| RU2009139076A (ru) | 2011-04-27 |
| WO2008118315A1 (en) | 2008-10-02 |
| EP2139849A4 (en) | 2012-07-04 |
| RU2471773C2 (ru) | 2013-01-10 |
| KR101572596B1 (ko) | 2015-11-27 |
| BRPI0809312A2 (pt) | 2014-10-14 |
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