JPS608688B2 - アクリルアミド系重合体の製造方法 - Google Patents
アクリルアミド系重合体の製造方法Info
- Publication number
- JPS608688B2 JPS608688B2 JP54073560A JP7356079A JPS608688B2 JP S608688 B2 JPS608688 B2 JP S608688B2 JP 54073560 A JP54073560 A JP 54073560A JP 7356079 A JP7356079 A JP 7356079A JP S608688 B2 JPS608688 B2 JP S608688B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerization
- polymer
- mercaptobenzimidazole
- water
- temperature
- 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
Links
- 229920002401 polyacrylamide Polymers 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 41
- 239000000178 monomer Substances 0.000 claims description 27
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 17
- 238000001035 drying Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 8
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 description 75
- 229920000642 polymer Polymers 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 239000003999 initiator Substances 0.000 description 18
- 239000012966 redox initiator Substances 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000006356 dehydrogenation reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- -1 oxygen radicals Chemical class 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MTPJEFOSTIKRSS-UHFFFAOYSA-N 3-(dimethylamino)propanenitrile Chemical compound CN(C)CCC#N MTPJEFOSTIKRSS-UHFFFAOYSA-N 0.000 description 3
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000004103 aminoalkyl group Chemical class 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000646858 Salix arbusculoides Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NXBBFAKHXAMPOM-UHFFFAOYSA-N n,n-dimethylprop-1-en-1-amine Chemical group CC=CN(C)C NXBBFAKHXAMPOM-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—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
- C08F6/00—Post-polymerisation treatments
- C08F6/06—Treatment of polymer solutions
- C08F6/12—Separation of polymers from solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Paper (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54073560A JPS608688B2 (ja) | 1979-06-13 | 1979-06-13 | アクリルアミド系重合体の製造方法 |
| US06/155,675 US4306045A (en) | 1979-06-13 | 1980-06-02 | Process for producing acrylamide polymers |
| DE3051131A DE3051131C2 (en, 2012) | 1979-06-13 | 1980-06-10 | |
| DE19803021767 DE3021767A1 (de) | 1979-06-13 | 1980-06-10 | Verfahren zur herstellung von acrylamidpolymeren |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54073560A JPS608688B2 (ja) | 1979-06-13 | 1979-06-13 | アクリルアミド系重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55165906A JPS55165906A (en) | 1980-12-24 |
| JPS608688B2 true JPS608688B2 (ja) | 1985-03-05 |
Family
ID=13521754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54073560A Expired JPS608688B2 (ja) | 1979-06-13 | 1979-06-13 | アクリルアミド系重合体の製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4306045A (en, 2012) |
| JP (1) | JPS608688B2 (en, 2012) |
| DE (2) | DE3021767A1 (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1356964A3 (ru) * | 1977-12-14 | 1987-11-30 | Нитто Кемикал Индастри Ко. Лтд (Фирма) | Способ стабилизации водного раствора полиакриламида или частично гидролизованного полиакриламида или сополимера акриламида с метакриловой кислотой |
| US4393163A (en) * | 1977-12-14 | 1983-07-12 | Nitto Chemical Industry, Co., Ltd. | Method for stabilizing an acrylamide polymer in a petroleum recovery process |
| US4426507A (en) | 1981-02-19 | 1984-01-17 | Kiselnikov Valentin N | Process for producing (co)-polymers from α,β unsaturated acid derivatives |
| US4561502A (en) * | 1982-01-07 | 1985-12-31 | Marathon Oil Company | Oil recovery process using a polyacrylamide gel |
| US4555558A (en) * | 1983-09-09 | 1985-11-26 | Nalco Chemical Company | Terpolymers of 2-acrylamido-2-methylpropane-sulfonic acid, sodium salt (AMPS), N,N-dimethylacrylamide, and acrylonitrile |
| US4963592A (en) * | 1989-11-20 | 1990-10-16 | The B. F. Goodrich Company | Super porous low molecular weight vinyl halide resins |
| DE69507067T2 (de) * | 1994-04-14 | 1999-08-05 | Mitsui Chemicals, Inc., Tokio/Tokyo | Verfahren zur Herstellung von hochmolekularen Acrylamidpolymeren |
| WO1997023519A1 (en) * | 1995-12-21 | 1997-07-03 | Ppg Industries, Inc. | Synthesis of aqueous, anionic, amino acrylate polymers |
| US5792331A (en) * | 1996-12-19 | 1998-08-11 | Dionex Corporation | Preformed polymer coating process and product |
| EP2933271B1 (de) | 2014-04-15 | 2016-03-23 | Basf Se | Verfahren zur herstellung von wasserlöslichen homo- oder copolymeren umfassend (meth)acrylamid |
| EP3059267B1 (en) | 2015-02-20 | 2017-11-29 | Basf Se | Process for producing stabilized polyacrylamides |
| MX2017010687A (es) | 2015-02-20 | 2017-11-17 | Basf Se | Proceso para producir composiciones de poliacrilamida estabilizadas. |
| US11001652B2 (en) | 2019-01-28 | 2021-05-11 | Alcon Inc. | High molecular weight poly(methacrylic acid) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1193635A (en) * | 1966-07-06 | 1970-06-03 | Edward Arthur Gill | Improvements in or relating to the Manufacture of Water-Soluble Synthetic Polymers |
| JPS5246276B2 (en, 2012) * | 1974-01-16 | 1977-11-22 | ||
| US4138446A (en) * | 1974-12-19 | 1979-02-06 | Sumitomo Chemical Company, Limited | Water-soluble high polymers and their preparation |
-
1979
- 1979-06-13 JP JP54073560A patent/JPS608688B2/ja not_active Expired
-
1980
- 1980-06-02 US US06/155,675 patent/US4306045A/en not_active Expired - Lifetime
- 1980-06-10 DE DE19803021767 patent/DE3021767A1/de active Granted
- 1980-06-10 DE DE3051131A patent/DE3051131C2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55165906A (en) | 1980-12-24 |
| US4306045A (en) | 1981-12-15 |
| DE3051131C2 (en, 2012) | 1991-09-26 |
| DE3021767C2 (en, 2012) | 1991-09-19 |
| DE3021767A1 (de) | 1980-12-18 |
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