JPH0127085B2 - - Google Patents
Info
- Publication number
- JPH0127085B2 JPH0127085B2 JP54014422A JP1442279A JPH0127085B2 JP H0127085 B2 JPH0127085 B2 JP H0127085B2 JP 54014422 A JP54014422 A JP 54014422A JP 1442279 A JP1442279 A JP 1442279A JP H0127085 B2 JPH0127085 B2 JP H0127085B2
- Authority
- JP
- Japan
- Prior art keywords
- chelatable
- polymerization
- impurity
- cationic species
- inert
- 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
- 238000006116 polymerization reaction Methods 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 35
- 239000012535 impurity Substances 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 25
- 125000002091 cationic group Chemical group 0.000 claims description 22
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical group OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 20
- 239000002738 chelating agent Substances 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- 239000003638 chemical reducing agent Substances 0.000 claims description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 11
- -1 azo compound Chemical class 0.000 claims description 11
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 9
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 229920003169 water-soluble polymer Polymers 0.000 claims description 6
- 230000000536 complexating effect Effects 0.000 claims description 5
- 229940050176 methyl chloride Drugs 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical group [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000011701 zinc Substances 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 13
- 150000002500 ions Chemical class 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 7
- 239000012736 aqueous medium Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 229910001447 ferric ion Inorganic materials 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001448 ferrous ion Inorganic materials 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 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
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 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
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical class 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940006486 zinc cation Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 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
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87714678A | 1978-02-13 | 1978-02-13 | |
| US05/909,320 US4145495A (en) | 1978-02-13 | 1978-05-24 | Aqueous free-radical polymerization using redox system initiator that avoids adverse effects of polymerization inhibiting cations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54120695A JPS54120695A (en) | 1979-09-19 |
| JPH0127085B2 true JPH0127085B2 (enrdf_load_stackoverflow) | 1989-05-26 |
Family
ID=27128432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1442279A Granted JPS54120695A (en) | 1978-02-13 | 1979-02-13 | Preparation of water soluble polymer |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS54120695A (enrdf_load_stackoverflow) |
| DE (1) | DE2905454C2 (enrdf_load_stackoverflow) |
| FI (1) | FI65625C (enrdf_load_stackoverflow) |
| FR (1) | FR2416902B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2014161B (enrdf_load_stackoverflow) |
| IT (1) | IT1115783B (enrdf_load_stackoverflow) |
| NL (1) | NL186166C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0593362U (ja) * | 1992-05-28 | 1993-12-21 | トーソー株式会社 | マグネットランナーとストッパーの組合せ |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB830011A (en) * | 1956-11-30 | 1960-03-09 | Courtaulds Ltd | Improvements in and relating to the polymerisation of vinyl compounds |
| US3332922A (en) * | 1963-05-13 | 1967-07-25 | Calgon Corp | Acrylamide polymers prepared in the presence of a redox catalyst system wherein a constant free-radical concentration is maintained |
| GB1193635A (en) * | 1966-07-06 | 1970-06-03 | Edward Arthur Gill | Improvements in or relating to the Manufacture of Water-Soluble Synthetic Polymers |
| GB1225983A (enrdf_load_stackoverflow) * | 1968-02-12 | 1971-03-24 | ||
| GB1279321A (en) * | 1969-03-31 | 1972-06-28 | Ici Ltd | New polymerisation process |
| US3573235A (en) * | 1969-09-22 | 1971-03-30 | Toyo Boseki | Polymerization of acrylonitrile in a concentrated solution of zinc chloride comprising the use of zinc sulfite as the reducing agent of a redox initiator |
| DE2139959A1 (de) * | 1971-08-10 | 1973-02-22 | Cassella Farbwerke Mainkur Ag | Verfahren zur herstellung von polymerisaten |
| BE791829A (fr) * | 1971-11-26 | 1973-05-23 | Bayer Ag | Filaments et fibres en chlorure de polyvinyle syndiotactique |
| ZA73603B (en) * | 1972-03-21 | 1974-09-25 | Lubrizol Corp | Improved acrylonitrile polymerization method and products thereof |
| JPS5144556B2 (enrdf_load_stackoverflow) * | 1973-01-25 | 1976-11-29 | ||
| JPS5945684B2 (ja) * | 1975-02-17 | 1984-11-08 | 第一工業製薬株式会社 | 水溶性アクリルアミド系重合体の製法 |
-
1978
- 1978-11-23 GB GB7845751A patent/GB2014161B/en not_active Expired
- 1978-12-08 NL NLAANVRAGE7812014,A patent/NL186166C/xx not_active IP Right Cessation
-
1979
- 1979-01-17 FI FI790143A patent/FI65625C/fi not_active IP Right Cessation
- 1979-02-01 IT IT47856/79A patent/IT1115783B/it active
- 1979-02-06 FR FR7903007A patent/FR2416902B1/fr not_active Expired
- 1979-02-13 JP JP1442279A patent/JPS54120695A/ja active Granted
- 1979-02-13 DE DE2905454A patent/DE2905454C2/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0593362U (ja) * | 1992-05-28 | 1993-12-21 | トーソー株式会社 | マグネットランナーとストッパーの組合せ |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1115783B (it) | 1986-02-03 |
| NL186166B (nl) | 1990-05-01 |
| IT7947856A0 (it) | 1979-02-01 |
| DE2905454A1 (de) | 1979-08-16 |
| GB2014161A (en) | 1979-08-22 |
| NL186166C (nl) | 1990-10-01 |
| NL7812014A (nl) | 1979-08-15 |
| DE2905454C2 (de) | 1985-05-09 |
| FI790143A7 (fi) | 1979-08-14 |
| FI65625C (fi) | 1984-06-11 |
| FI65625B (fi) | 1984-02-29 |
| FR2416902B1 (fr) | 1986-03-21 |
| JPS54120695A (en) | 1979-09-19 |
| FR2416902A1 (fr) | 1979-09-07 |
| GB2014161B (en) | 1982-05-19 |
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