RU2734916C9 - Способ получения катионного полимера с по меньшей мере бимодальным распределением молекулярной массы - Google Patents
Способ получения катионного полимера с по меньшей мере бимодальным распределением молекулярной массы Download PDFInfo
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- RU2734916C9 RU2734916C9 RU2018130687A RU2018130687A RU2734916C9 RU 2734916 C9 RU2734916 C9 RU 2734916C9 RU 2018130687 A RU2018130687 A RU 2018130687A RU 2018130687 A RU2018130687 A RU 2018130687A RU 2734916 C9 RU2734916 C9 RU 2734916C9
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- monomer
- monomer component
- cationic polymer
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- 229920006317 cationic polymer Polymers 0.000 title claims abstract description 123
- 238000000034 method Methods 0.000 title claims abstract description 83
- 238000009826 distribution Methods 0.000 title claims abstract description 22
- 230000002902 bimodal effect Effects 0.000 title claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 196
- 229920000642 polymer Polymers 0.000 claims abstract description 85
- 238000004062 sedimentation Methods 0.000 claims abstract description 36
- 125000002091 cationic group Chemical group 0.000 claims abstract description 35
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 27
- 230000008569 process Effects 0.000 claims abstract description 27
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 16
- 239000012071 phase Substances 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 77
- 238000006116 polymerization reaction Methods 0.000 claims description 77
- 239000003921 oil Substances 0.000 claims description 70
- -1 allyl acrylates Chemical class 0.000 claims description 53
- 239000003381 stabilizer Substances 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000012190 activator Substances 0.000 claims description 30
- 239000006185 dispersion Substances 0.000 claims description 30
- 239000003999 initiator Substances 0.000 claims description 27
- 239000007762 w/o emulsion Substances 0.000 claims description 27
- 239000008346 aqueous phase Substances 0.000 claims description 25
- 238000009835 boiling Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 238000012688 inverse emulsion polymerization Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 230000000379 polymerizing effect Effects 0.000 claims description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 12
- 235000019253 formic acid Nutrition 0.000 claims description 12
- 230000002209 hydrophobic effect Effects 0.000 claims description 12
- 229920003169 water-soluble polymer Polymers 0.000 claims description 12
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 7
- 229930006000 Sucrose Natural products 0.000 claims description 7
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 7
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 claims description 7
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 7
- 239000005720 sucrose Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical group C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 claims description 4
- FYRWKWGEFZTOQI-UHFFFAOYSA-N 3-prop-2-enoxy-2,2-bis(prop-2-enoxymethyl)propan-1-ol Chemical compound C=CCOCC(CO)(COCC=C)COCC=C FYRWKWGEFZTOQI-UHFFFAOYSA-N 0.000 claims description 4
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005399 allylmethacrylate group Chemical group 0.000 claims description 3
- 239000008139 complexing agent Substances 0.000 claims description 3
- 239000004815 dispersion polymer Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- 229920000151 polyglycol Polymers 0.000 claims description 3
- 239000010695 polyglycol Substances 0.000 claims description 3
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 claims description 3
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims description 3
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- LVKKFNORSNCNPP-UHFFFAOYSA-N 2,2-bis(prop-2-enoylamino)acetic acid Chemical compound C=CC(=O)NC(C(=O)O)NC(=O)C=C LVKKFNORSNCNPP-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000004386 diacrylate group Chemical group 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000002904 solvent Substances 0.000 description 57
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 52
- 239000007864 aqueous solution Substances 0.000 description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- 150000002191 fatty alcohols Chemical class 0.000 description 37
- 239000000839 emulsion Substances 0.000 description 32
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 29
- 238000002156 mixing Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000003995 emulsifying agent Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 20
- 229940001584 sodium metabisulfite Drugs 0.000 description 20
- 235000010262 sodium metabisulphite Nutrition 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 19
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- 235000014113 dietary fatty acids Nutrition 0.000 description 18
- 229930195729 fatty acid Natural products 0.000 description 18
- 239000000194 fatty acid Substances 0.000 description 18
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 16
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
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- 239000002979 fabric softener Substances 0.000 description 14
- 150000002430 hydrocarbons Chemical class 0.000 description 14
- OPJWPPVYCOPDCM-UHFFFAOYSA-N 2-ethylhexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CC)CCCC OPJWPPVYCOPDCM-UHFFFAOYSA-N 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 13
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- XUQOHDOVMVGYSM-UHFFFAOYSA-N 2-methylprop-2-enoic acid;octadecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(O)=O.CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C XUQOHDOVMVGYSM-UHFFFAOYSA-N 0.000 description 12
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- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 11
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 9
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- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
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- HKILWKSIMZSWQX-UHFFFAOYSA-N tris(prop-2-enyl)silane Chemical compound C=CC[SiH](CC=C)CC=C HKILWKSIMZSWQX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08F220/56—Acrylamide; Methacrylamide
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- 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
-
- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
-
- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- 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
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F226/08—N-Vinyl-pyrrolidine
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- C08F226/10—N-Vinyl-pyrrolidone
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or 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; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
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- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/05—Bimodal or multimodal molecular weight distribution
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- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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| PCT/EP2017/050829 WO2017129434A1 (en) | 2016-01-25 | 2017-01-16 | A process for obtaining a cationic polymer with an at least bimodal molecular weight distribution |
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| ES2770765T3 (es) * | 2016-01-25 | 2020-07-03 | Basf Se | Polímero catiónico con una distribución de peso molecular al menos bimodal |
| FR3079833B1 (fr) | 2018-04-10 | 2020-10-09 | Rhodia Operations | Composition aqueuse gelifiee pour l'extraction petroliere |
| FR3096985B1 (fr) * | 2019-06-05 | 2021-05-14 | S N F Sa | Procede de preparation de polymeres structures sous forme de poudre par voie gel |
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- 2017-01-16 CA CA3009585A patent/CA3009585A1/en not_active Abandoned
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| RU2183646C2 (ru) * | 1996-10-03 | 2002-06-20 | Сайтек Текнолоджи Корп. | Водные дисперсии |
| WO2004050815A1 (en) * | 2002-11-29 | 2004-06-17 | Ciba Specialty Chemicals Holding Inc. | Aqueous compositions comprising homo- and/ or copolymers |
| RU2394846C2 (ru) * | 2004-12-28 | 2010-07-20 | Акцо Нобель Н.В. | Дисперсия полимера и способ получения дисперсии полимера |
| WO2013174622A1 (en) * | 2012-05-21 | 2013-11-28 | Basf Se | Inverse dispersion comprising a cationic polymer and a stabilizing agent |
| RU2560177C1 (ru) * | 2014-10-16 | 2015-08-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) | Способ получения водорастворимых полимеров на основе четвертичных солей диметиламиноэтилметакрилата |
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| US10920001B2 (en) | 2021-02-16 |
| EP3408301B1 (en) | 2020-03-11 |
| WO2017129434A1 (en) | 2017-08-03 |
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| MX2018009117A (es) | 2018-11-09 |
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| EP3408301A1 (en) | 2018-12-05 |
| BR112018014989A2 (en) | 2018-12-11 |
| PL3408301T3 (pl) | 2020-08-24 |
| JP7068190B2 (ja) | 2022-05-16 |
| RU2018130687A (ru) | 2020-02-27 |
| RU2734916C2 (ru) | 2020-10-26 |
| CN108602902A (zh) | 2018-09-28 |
| RU2018130687A3 (enExample) | 2020-03-25 |
| KR20180104298A (ko) | 2018-09-20 |
| JP2019505657A (ja) | 2019-02-28 |
| BR112018014989B1 (pt) | 2022-06-28 |
| CA3009585A1 (en) | 2017-08-03 |
| CN108602902B (zh) | 2021-06-04 |
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