CA1286448C - Flocculating agents based upon copolymers of acrylamide and dimethylaminopropylacrylamide for use in dewatering sludge - Google Patents
Flocculating agents based upon copolymers of acrylamide and dimethylaminopropylacrylamide for use in dewatering sludgeInfo
- Publication number
- CA1286448C CA1286448C CA000525473A CA525473A CA1286448C CA 1286448 C CA1286448 C CA 1286448C CA 000525473 A CA000525473 A CA 000525473A CA 525473 A CA525473 A CA 525473A CA 1286448 C CA1286448 C CA 1286448C
- Authority
- CA
- Canada
- Prior art keywords
- copolymer
- dimethylaminopropylacrylamide
- acrylamide
- copolymers
- process according
- 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 - Lifetime
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 32
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 title claims abstract description 17
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000010802 sludge Substances 0.000 title claims abstract description 15
- 239000008394 flocculating agent Substances 0.000 title claims abstract description 12
- 125000002091 cationic group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 230000001588 bifunctional effect Effects 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 229920000867 polyelectrolyte Polymers 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 150000001450 anions Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 3
- 239000002440 industrial waste Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229920000642 polymer Polymers 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 230000003311 flocculating effect Effects 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- GNGACRATGGDKBX-UHFFFAOYSA-N dihydroxyacetone phosphate Chemical compound OCC(=O)COP(O)(O)=O GNGACRATGGDKBX-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 101000962156 Homo sapiens N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase Proteins 0.000 description 3
- LZCXCXDOGAEFQX-UHFFFAOYSA-N N-Acryloylglycine Chemical compound OC(=O)CNC(=O)C=C LZCXCXDOGAEFQX-UHFFFAOYSA-N 0.000 description 3
- 102100039267 N-acetylglucosamine-1-phosphodiester alpha-N-acetylglucosaminidase Human genes 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005189 flocculation Methods 0.000 description 3
- 230000016615 flocculation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 239000010801 sewage sludge Substances 0.000 description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- 102100022749 Aminopeptidase N Human genes 0.000 description 1
- 101710099461 Aminopeptidase N Proteins 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- 208000010201 Exanthema Diseases 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
- 241000282320 Panthera leo Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229920003118 cationic copolymer Polymers 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000007 visual effect Effects 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
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
- Treatment Of Sludge (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3544909.8-44 | 1985-12-19 | ||
| DE19853544909 DE3544909A1 (de) | 1985-12-19 | 1985-12-19 | Copolymere aus acrylamid und dimethylaminopropylacrylamid als flockungsmittel und verfahren zum entwaessern von klaerschlaemmen unter verwendung dieser flockungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1286448C true CA1286448C (en) | 1991-07-16 |
Family
ID=6288833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000525473A Expired - Lifetime CA1286448C (en) | 1985-12-19 | 1986-12-16 | Flocculating agents based upon copolymers of acrylamide and dimethylaminopropylacrylamide for use in dewatering sludge |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5512646A (en, 2012) |
| EP (1) | EP0228637B1 (en, 2012) |
| JP (1) | JPH0763720B2 (en, 2012) |
| AT (1) | ATE53597T1 (en, 2012) |
| AU (1) | AU584765B2 (en, 2012) |
| CA (1) | CA1286448C (en, 2012) |
| DE (2) | DE3544909A1 (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63234007A (ja) * | 1987-03-23 | 1988-09-29 | Kohjin Co Ltd | 水溶性が良好なカチオン性重合体 |
| DE3905049A1 (de) * | 1989-02-18 | 1990-08-23 | Stockhausen Chem Fab Gmbh | Verfahren zur stoerstoffixierung bei der papierherstellung |
| US4981936A (en) * | 1989-04-14 | 1991-01-01 | Polypure, Inc. | Terpolymer of oxyalkyene acrylates, acrylamides and quaternary monomers |
| DE10119685A1 (de) * | 2001-04-20 | 2002-10-24 | Stockhausen Chem Fab Gmbh | Entfernung nicht-wasserlöslicher Substanzen aus Metallaufschlüssen |
| DE10333478A1 (de) | 2003-07-22 | 2005-03-10 | Stockhausen Chem Fab Gmbh | Verfahren zur Behandlung von wässrigem Schlamm, danach hergestelltes Material und dessen Verwendung |
| DE10337763A1 (de) * | 2003-08-14 | 2005-03-17 | Stockhausen Gmbh | Pulverförmige, wasserlösliche kationische Polymerzusammensetzung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10337764A1 (de) * | 2003-08-14 | 2005-03-17 | Stockhausen Gmbh | Pulverförmige, wasserlösliche kationische Polymerzusammensetzung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CN100528951C (zh) * | 2003-12-15 | 2009-08-19 | 吸收剂科技有限公司 | 一种含有具生物活性的促生长添加剂的超吸收聚合物产品的制造和使用方法 |
| US7425595B2 (en) * | 2003-12-15 | 2008-09-16 | Absorbent Technologies, Inc. | Superabsorbent polymer products including a beneficial additive and methods of making and application |
| US20050261399A1 (en) * | 2004-05-19 | 2005-11-24 | David Hunkeler | Powdered flocculants prepared by using evaporative cooling to coat polymeric materials on a porous substrate |
| EP1781709A4 (en) * | 2004-08-27 | 2011-07-06 | Absorbent Technologies Inc | SUPER ABSORBING POLYMERS IN AGRICULTURAL APPLICATIONS |
| US20070167330A1 (en) * | 2006-01-17 | 2007-07-19 | Savich Milan H | Superabsorbent polymer applicator |
| US20070163172A1 (en) * | 2006-01-17 | 2007-07-19 | Savich Milan H | Biodegradable mat containing superabsorbent polymers |
| US7607259B2 (en) * | 2006-01-17 | 2009-10-27 | Absorbent Technologies, Inc. | Superabsorbent polymer root dip |
| US8343469B2 (en) | 2009-07-02 | 2013-01-01 | Hercules Incorporated | Cationic synthetic polymers with improved solubility and performance in surfactant-based systems and use in personal care and household applications |
| US8568701B2 (en) | 2009-07-02 | 2013-10-29 | Hercules Incorporated | Cationic synthetic polymers with improved solubility and performance in phosphate surfactant-based systems and use in personal care and household applications |
| DE102010019375A1 (de) * | 2010-05-04 | 2011-11-10 | Crenox Gmbh | Flockungshilfsmittel für die Titandioxidherstellung |
| US9596801B2 (en) | 2010-10-25 | 2017-03-21 | Vjs Investments Limited | Superabsorbent polymer seed coatings and associated methods |
| US11730193B2 (en) | 2019-12-15 | 2023-08-22 | Shaheen Innovations Holding Limited | Hookah device |
| CN111392806B (zh) * | 2020-03-24 | 2022-11-08 | 山东鑫泰水处理技术股份有限公司 | 一种印染废水复合脱色剂及其制备方法 |
| CN112940178B (zh) * | 2021-02-03 | 2022-10-14 | 中国海洋石油集团有限公司 | 一种可降解清水剂的应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014896A (en) * | 1956-10-17 | 1961-12-26 | Union Carbide Corp | Polymeric flocculating agents and process for the production thereof |
| US3661868A (en) * | 1970-05-01 | 1972-05-09 | Dow Chemical Co | Flocculant |
| JPS529093A (en) * | 1975-07-10 | 1977-01-24 | Sumitomo Chem Co Ltd | Preparation of water-soluble cationic high-polymer |
| FR2471391A1 (fr) * | 1979-12-14 | 1981-06-19 | Hoechst France | Polyelectrolytes cationiques forts, en poudre, a base d'acrylamide et d'acrylate de dimethylaminoethyle quaternise ou salifie et leur utilisation pour la floculation des suspensions de matieres solides et la coalescence des emulsions |
| FR2390983A1 (fr) * | 1977-05-16 | 1978-12-15 | Hoechst France | Polyelectrolytes cationiques en poudre, a base d'acrylamide et d'acrylate de dimethyl-aminoethyle quaternise ou salifie, leur procede d'obtention et leur utilisation |
| DE2848627C2 (de) * | 1978-11-09 | 1982-02-04 | Röhm GmbH, 6100 Darmstadt | Verfahren zur Herstellung eines flüssigen, unmittelbar polymerisierbaren Gemisches aus Acrylamid und Quaternierungsprodukten von tertiären Aminoalkylestern oder tertiären Aminoalkylamiden der Acryl- oder Methacrylsäure |
| JPS5571703A (en) * | 1978-11-25 | 1980-05-30 | Sanyo Chem Ind Ltd | Preparation of water-soluble particulate polymer |
| EP0038573B1 (de) * | 1978-12-27 | 1985-09-04 | Chemische Fabrik Stockhausen GmbH | Polymerisate von alpha,beta-ungesättigten N-substituierten Carbonsäureamiden und ihre Verwendung als Sedimentations-, Flockungs-, Entwässerungs- und Retentionshilfsmittel |
| JPS5681315A (en) * | 1979-12-07 | 1981-07-03 | Mitsubishi Chem Ind Ltd | Production of water-soluble bead polymer |
| US4297256A (en) * | 1979-12-26 | 1981-10-27 | The Dow Chemical Company | Preparation of water-immiscible, acid-soluble N-(aminomethyl)-α,.beta. |
| JPS5849410A (ja) * | 1981-09-19 | 1983-03-23 | Sanyo Chem Ind Ltd | カチオン性高分子凝集剤 |
| JPS5924708A (ja) * | 1982-08-02 | 1984-02-08 | Kohjin Co Ltd | アクリルアミド系カチオン性重合体の製造方法 |
| JPS59135212A (ja) * | 1983-01-24 | 1984-08-03 | Nitto Chem Ind Co Ltd | カチオン性重合体の製造方法 |
| JPS59193911A (ja) * | 1983-04-18 | 1984-11-02 | Kohjin Co Ltd | 高吸収性高分子物質 |
| DE3327600A1 (de) * | 1983-07-30 | 1985-02-14 | Sandoz-Patent-GmbH, 7850 Lörrach | Copolymerisat- und tensidhaltige praeparate, deren herstellung und verwendung |
| JPS60210608A (ja) * | 1984-04-04 | 1985-10-23 | Mitsui Toatsu Chem Inc | 水溶性高分子量重合体粉末の製造方法 |
| JPH0794502B2 (ja) * | 1984-05-15 | 1995-10-11 | 三井東圧化学株式会社 | 水溶性高分子量重合体粉末の製造方法 |
| GB8512937D0 (en) * | 1985-05-22 | 1985-06-26 | Allied Colloids Ltd | Water treatment |
| DE3624813A1 (de) * | 1986-07-23 | 1988-03-10 | Stockhausen Chem Fab Gmbh | Amphotere wasserloesliche polymere, verfahren zu ihrer herstellung und ihre verwendung als dispergierhilfsmittel |
-
1985
- 1985-12-19 DE DE19853544909 patent/DE3544909A1/de active Granted
-
1986
- 1986-12-12 DE DE8686117354T patent/DE3671900D1/de not_active Expired - Lifetime
- 1986-12-12 EP EP86117354A patent/EP0228637B1/de not_active Expired - Lifetime
- 1986-12-12 AT AT86117354T patent/ATE53597T1/de not_active IP Right Cessation
- 1986-12-16 AU AU66576/86A patent/AU584765B2/en not_active Ceased
- 1986-12-16 CA CA000525473A patent/CA1286448C/en not_active Expired - Lifetime
- 1986-12-17 JP JP61299053A patent/JPH0763720B2/ja not_active Expired - Lifetime
-
1993
- 1993-09-13 US US08/120,707 patent/US5512646A/en not_active Expired - Lifetime
-
1997
- 1997-05-27 US US08/863,999 patent/US6228964B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0228637A3 (en) | 1987-09-23 |
| AU584765B2 (en) | 1989-06-01 |
| US6228964B1 (en) | 2001-05-08 |
| DE3544909A1 (de) | 1987-06-25 |
| EP0228637B1 (de) | 1990-06-13 |
| DE3544909C2 (en, 2012) | 1991-10-24 |
| ATE53597T1 (de) | 1990-06-15 |
| DE3671900D1 (de) | 1990-07-19 |
| EP0228637A2 (de) | 1987-07-15 |
| JPS62201915A (ja) | 1987-09-05 |
| JPH0763720B2 (ja) | 1995-07-12 |
| AU6657686A (en) | 1987-06-25 |
| US5512646A (en) | 1996-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |