WO1990006336A1 - Polyelectrolytes modified by reaction with anhydride group containing copolymers and their use as flocculents - Google Patents
Polyelectrolytes modified by reaction with anhydride group containing copolymers and their use as flocculents Download PDFInfo
- Publication number
- WO1990006336A1 WO1990006336A1 PCT/AU1989/000523 AU8900523W WO9006336A1 WO 1990006336 A1 WO1990006336 A1 WO 1990006336A1 AU 8900523 W AU8900523 W AU 8900523W WO 9006336 A1 WO9006336 A1 WO 9006336A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyelectrolyte
- process according
- copolymer
- modified
- reaction
- Prior art date
Links
- 229920000867 polyelectrolyte Polymers 0.000 title claims abstract description 67
- 238000006243 chemical reaction Methods 0.000 title claims description 29
- 229920001577 copolymer Polymers 0.000 title claims description 27
- 150000008064 anhydrides Chemical group 0.000 title claims description 7
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 14
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 14
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 230000003311 flocculating effect Effects 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- -1 vinyl pyrollidone Chemical compound 0.000 claims description 5
- 238000005189 flocculation Methods 0.000 claims description 3
- 230000016615 flocculation Effects 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000004018 acid anhydride group Chemical group 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229920005601 base polymer Polymers 0.000 description 14
- 239000003245 coal Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 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
- 239000004816 latex Substances 0.000 description 5
- 229920000126 latex Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229940117913 acrylamide Drugs 0.000 description 4
- 239000008394 flocculating agent Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005065 mining Methods 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- JHRWWRDRBPCWTF-UHFFFAOYSA-N captafol Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)C21 JHRWWRDRBPCWTF-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
Definitions
- the present invention relates to modified polyelectrolytes which are useful as flocculents 1n separation processes, to processes for preparing the modified polyelectrolytes, flocculent compositions Incorporating the modified polyelectrolytes and to separation methods employing the modified
- the modified polyelectrolytes of the Invention perform better than the prior art polyelectrolytes in that they are capable of achieving the same level of flocculation at lower concentrations and are capable of retaining a higher percentage of super fines.
- Practical synthetic organic flocculants are water soluble polymeric substances with weight average molecular weights ranging from about 1000 to greater than 5 million (reported values as high as 20 million).
- Polyelectrolytes used as flocculants include polymers and copolymers made from a number of monomers including maleic anhydride, maleic add, acrylic acid, acrylamlde, acrylonitrile, methacrylic acid, vinyl sulfonlc acid, p-styrene sulfonic acid, styrene, vinyl methyl ether, metaphosphorlc add, vinylamine, ethyleneimine, vinyl pyri di ne and 4-vinyl-N- dodecylpyrldinium chloride.
- a modified polyelectrolyte characterized in that a polyelectrolyte is reacted with a copolymer of at least two ethylenically unsaturated monomers, at least one of which contains anhydride groups.
- a process for manufacturing a modified polyelectrolyte comprises reacting a polyelectrolyte with a copolymer of at least 2 ethylenically unsaturated monomers, at least one of which contains add anhydride groups.
- the reaction can be initiated by heat and/or by an inorganic accelarator such as a metallic base.
- a suitable accelerator is potassium carbonate.
- polyelectrolytes suitable for use in this invention are extremely numerous and diversified. No unsuitable commercially available or laboratory synthesized polyelectrolyte has been found. Common trade names defining such polyelectrolytes include: SANYOFLOC; ALFLOC; SUPERFLOC;
- the polyelectrolytes which can be modified according to the invention have molecular weights in the range 2x10 4 to 1x10 8 , especially 1x10 5 to 7x10 6 daltons.
- polyelectrolytes are reacted have molecular weights in the range 1x10 4 to
- a known polyelectrolyte flocculant is reacted with a copolymer of methyl vinyl ether and maleic anhydride.
- a third embodiment of the invention provides a further modified polyelectrolyte characterized in that the modified polymer according to the first embodiment of the invention is further modified by reaction with vinyl pyrrolidone or polyvinyl pyrrolidone followed by further reaction with the copolymer.
- a fourth embodiment of the invention provides a process for manufacturing a further modified polyelectrolyte which process comprises terminating the process according to the second embodiment of the invention by reducing the temperature, dispersing the reaction mixture with v inyl
- the further reaction can also be Initiated by heat and/or by an Inorganic accelerator.
- a fifth embodiment of the invention provides a flocculating composition
- a flocculating composition comprising a modified polyelectrolyte or a further modified polyelectrolyte according to the invention in association with the usual carriers and diluent employed in conventional flocculating compositions.
- a sixth embodiment of the invention provides a method of flocculation which method comprises adding to a material to be flocculated a modified polyelectrolyte, a further modified electrolyte and/or a flocculating composition according to the invention.
- Polymer solids at an amount of between 0 and 200%, preferably 10%. by weight (on the basis of polyelectrolyte solids) may effectively be employed in this invention.
- reaction is carried out by simple mixing or
- reaction times and reaction temperatures will depend on the nature of the polyelectrolyte and the copolymer but generally the reaction can be carried out at temperature of between 0° and 120oC for a time of between 5 minutes to 4 hours. It is preferred that the polyelectrolyte and copolymer be selected such that the reaction can be carried out at a temperature of between 40° and 80oC for a time of up to 50 minutes. Preferably, the reaction is carried out in solution.
- the reaction is stopped, preferably by reducing the temperature to below 30oC, vinyl pyrrol idone or polyvinyl pyrrolidone is added, the mixture is agitated or stirred to disperse the vinyl pyrrolidone or polyvinyl pyrrolidone and the mixture is reheated to restart the reaction. If there is an excess of copolymer, the vinyl pyrrolidone or polyvinyl pyrrolidone is added, the mixture is agitated or stirred to disperse the vinyl pyrrolidone or polyvinyl pyrrolidone and the mixture is reheated to restart the reaction. If there is an excess of copolymer, the vinyl
- polyvinyl pyrrolidone reacts with the anhydride moiety of either reacted or unreacted copolymer resulting in a mixture of further modified polyelectrolyte and modified copolymer.
- the ratio of vinyl pyrrolidone or polyvinyl pyrrolidone to copolymer is in the range 1:1 to 1:10 by weight, more
- the amounts of poly(methyl vinyl ether/maleic anhydride) were varied between 0 to 100% of the solids of base polyelectrolytes.
- polymer solids (based on polyelectrolyte solids) with molecular weight of poly(methyl vinyl ether/maleic anhydride) at 67,000 daltons.
- Example 2 is based on the above percentage and molecular weight.
- the base polymer number refers to Table 1.
- Example 1 The polymers prepared in Example 1 were evaluated for efficiency by comparison with the polyelectrolytes from which they were derived. In all cases the performance of the new materials was superior to that of the polyelectrolytes from which they were derived. Comparisons conducted at mine sites were advantageously done by selecting a polyelectrolyte with correct charge density for the materials being separated and comparing these with modified polyelectrolytes comprising the same base
- a Latex polymer of the following characteristics was prepared.
- This polymer was cooled to below 30oC then further reacted with 1.5% by weight poly(methyl vinyl ether/maleic anhydride) with a mw 80,000
- the reaction was carried out by dispersing the powder through the latex and placing into a water bath at 50oC for 50 minutes. On cooling the flocculent latex was packaged.
- a solution polymer of the following characteristics was cooked.
- This polymer was reacted with 0.5% polymer (methyl vinyl ether/maleic anhydride) with a mw of 67000 daltons(ex GAF).
- the reaction was carried out by dispersing the powder through the solution and placing into a water bath at 60°C for 4 hours. The resultant mixture was cooled to below 30oC and 1.0% of polyvinyl pyroll idone was dispersed into the mixture. The mixture was replaced into the water bath for 2 hours. On cooling the flocculent solution was packaged.
- a latex polymer of the following characteristics was prepared. Organic solids 28.5% pH(1%) 8.0
- Ratio Acrylamide:Acrylic Acid 34 23 nominal mw 12x10 6
- This polymer was cooled to below 30°C then further reacted with 2.5% by weight of poly(methyl vinyl ether/maleic anhydride) mw 67,000 (daltons) dispersed in twice Its weight of 1n aromatic solvent.
- This mixture was cooled to below 30oC and 0.5% of polyvinyl pyrrolidone was dispersed in the mixture. The mixture was replaced Into the water bath for 30 min. On cooling the flocculent latex was packaged.
- a solution polymer of the following characteristics was prepared.
- This polymer was reacted with 0.57. poly(methyl vinyl ether/mlleic anhydride) with a mw 80,000 daltons.
- the reaction was carried out by dispersing the powder through the solution and placing Into a water bath at 60°C for 4 hours. The resultant mixture was cooled to below 30°C and 0.1% of polyvinyl pyrrolidone was dispersed in the mixture. The mixture was replaced into the water bath for 2 hours. On cooling the flocculent solution was packaged.
- a solution polymer of the following characteristics was prepared.
- This base polymer was reacted with 0.5% w/w poly(methyl vinyl ether/ maleic anhydride) with a mw of 67,000 daltons.
- the reaction was carried out by dispersing the powder through the solution and placing into a sealed container in a water bath for 4 hours at 60°C.
- the resultant mixture was cooled to below 30C and 0.1% of polyvinyl pyrrolidone was dispersed in the mixture.
- the mixture was replaced into the water bath for.2 hours. On cooling the flocculent solution was packaged.
- a solution polymer of the following characteristics was prepared.
- This base polymer was reacted with 0.57. poly(methyl vinyl ether/maleic anhydride) with a mw of 67,000 daltons.
- the reaction was carried out by dispersing the powder through the solution and placing it into a sealed container in a water bath for 4 hours at 60oC.
- the resultant mixture was cooled to below 30oC and 0.1% of polyvinyl pyrrolidone was dispersed in the mixture.
- the mixture was replaced Into the water bath for 2 hours. On cooling the flocculent solution was packaged.
- the present invention provides modified polyelectrolytes which are useful as flocculents and find use in separation processes from fields as diverse as water treatment, oil refining, metal finishing, food processing, paper milling, mineral processing and manufacturing processes.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental & Geological Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Water Supply & Treatment (AREA)
- Engineering & Computer Science (AREA)
- Hydrology & Water Resources (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO90903427A NO903427L (no) | 1988-12-05 | 1990-08-03 | Polyelektrolytter, modifisert ved omsetning med anhydridgruppeholdige kopolymerer, og deres anvendelse som flokkuleringsmidler. |
| DK186090A DK186090A (da) | 1988-12-05 | 1990-08-03 | Polyelektrolytter, der er modificeret med anhydridgruppeholdige copolymerer, og anvendelse af saadanne polyelektrolytter som flokkulationsmidler |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPJ1806 | 1988-12-05 | ||
| AUPJ1807 | 1988-12-05 | ||
| AUPJ180688 | 1988-12-05 | ||
| AUPJ180788 | 1988-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1990006336A1 true WO1990006336A1 (en) | 1990-06-14 |
Family
ID=25643589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/AU1989/000523 WO1990006336A1 (en) | 1988-12-05 | 1989-12-04 | Polyelectrolytes modified by reaction with anhydride group containing copolymers and their use as flocculents |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0400129A4 (forum.php) |
| JP (1) | JPH03503295A (forum.php) |
| CN (2) | CN1043298A (forum.php) |
| CA (1) | CA2004549A1 (forum.php) |
| DK (1) | DK186090A (forum.php) |
| IL (1) | IL92554A0 (forum.php) |
| IN (1) | IN176443B (forum.php) |
| MY (1) | MY105082A (forum.php) |
| WO (1) | WO1990006336A1 (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5560353A (en) * | 1992-07-23 | 1996-10-01 | Taema | Equipment and process for supplying doses of at least one gas to the respiratory tracts of a user |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011032253A1 (en) | 2009-09-15 | 2011-03-24 | Suncor Energy Inc. | Process for drying oil sand mature fine tailings |
| CA3050234C (en) | 2009-09-15 | 2022-11-08 | Suncor Energy Inc. | Techniques for flocculating and dewatering fine tailings |
| AU2009354586A1 (en) | 2009-10-30 | 2012-05-24 | Suncor Energy Inc. | Depositing and farming methods for drying oil sand mature fine tailings |
| CN111483654A (zh) * | 2020-05-08 | 2020-08-04 | 胡艳锋 | 一种果蔬自动包装机用封箱装置 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1133910A (en) * | 1964-01-27 | 1968-11-20 | Amicon Corp | Modified polyelectrolyte composition and method of making same |
| GB1293464A (en) * | 1969-02-07 | 1972-10-18 | Mobil Oil Corp | Liquid hydrocarbon compositions containing reaction products of amine derivatives of ethylenically unsaturated hydrocarbon maleic anhydride copolymers and methyl vinyl ether/maleic anhydride copolymers as anti-static agents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5611775B2 (forum.php) * | 1972-09-11 | 1981-03-17 | ||
| US4255309A (en) * | 1979-08-16 | 1981-03-10 | Betz Laboratories, Inc. | Polyacrylic acids and methyl vinyl ether/maleic anhydride copolymers as soft scale inhibitors |
| JPS6383150A (ja) * | 1986-09-29 | 1988-04-13 | Mitsubishi Petrochem Co Ltd | 吸水性樹脂組成物およびその製造法 |
-
1989
- 1989-12-04 MY MYPI89001693A patent/MY105082A/en unknown
- 1989-12-04 EP EP19900900031 patent/EP0400129A4/en not_active Withdrawn
- 1989-12-04 CA CA002004549A patent/CA2004549A1/en not_active Abandoned
- 1989-12-04 JP JP2500110A patent/JPH03503295A/ja not_active Withdrawn
- 1989-12-04 WO PCT/AU1989/000523 patent/WO1990006336A1/en not_active Application Discontinuation
- 1989-12-05 CN CN89109764.3A patent/CN1043298A/zh active Pending
- 1989-12-05 IN IN1142DE1989 patent/IN176443B/en unknown
- 1989-12-05 IL IL92554A patent/IL92554A0/xx not_active IP Right Cessation
-
1990
- 1990-08-03 DK DK186090A patent/DK186090A/da not_active Application Discontinuation
-
1995
- 1995-03-17 CN CN95100572.3A patent/CN1112906A/zh active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1133910A (en) * | 1964-01-27 | 1968-11-20 | Amicon Corp | Modified polyelectrolyte composition and method of making same |
| GB1293464A (en) * | 1969-02-07 | 1972-10-18 | Mobil Oil Corp | Liquid hydrocarbon compositions containing reaction products of amine derivatives of ethylenically unsaturated hydrocarbon maleic anhydride copolymers and methyl vinyl ether/maleic anhydride copolymers as anti-static agents |
Non-Patent Citations (3)
| Title |
|---|
| PATENTS ABSTRACTS OF JAPAN, C-523, page 93, JP, A, 63-83150 (Mitsubishi Pertochem Co Ltd) 13 April 1988 (13. 04. 88) * |
| PATENTS ABSTRACTS of JAPAN, C-79, page 24, JP, A, 56-103203 (Otsuka Kagaku Yakuhin K.K.) 18 August 1981 (18.08.81) * |
| See also references of EP0400129A4 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5560353A (en) * | 1992-07-23 | 1996-10-01 | Taema | Equipment and process for supplying doses of at least one gas to the respiratory tracts of a user |
Also Published As
| Publication number | Publication date |
|---|---|
| IL92554A0 (en) | 1990-08-31 |
| EP0400129A4 (en) | 1992-05-06 |
| IN176443B (forum.php) | 1996-05-25 |
| EP0400129A1 (en) | 1990-12-05 |
| CA2004549A1 (en) | 1990-06-05 |
| DK186090D0 (da) | 1990-08-03 |
| DK186090A (da) | 1990-08-03 |
| CN1112906A (zh) | 1995-12-06 |
| JPH03503295A (ja) | 1991-07-25 |
| MY105082A (en) | 1994-08-30 |
| CN1043298A (zh) | 1990-06-27 |
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