JPS61118406A - 水溶性ポリビニルアミンの製造方法 - Google Patents
水溶性ポリビニルアミンの製造方法Info
- Publication number
- JPS61118406A JPS61118406A JP24029884A JP24029884A JPS61118406A JP S61118406 A JPS61118406 A JP S61118406A JP 24029884 A JP24029884 A JP 24029884A JP 24029884 A JP24029884 A JP 24029884A JP S61118406 A JPS61118406 A JP S61118406A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- water
- hydrolysis
- vinylformamide
- ammonia
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 229920000642 polymer Polymers 0.000 claims abstract description 35
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 24
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 230000007062 hydrolysis Effects 0.000 claims abstract description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 125000003368 amide group Chemical group 0.000 abstract description 3
- 150000003335 secondary amines Chemical class 0.000 abstract description 3
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 239000010802 sludge Substances 0.000 abstract description 2
- 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 abstract 1
- 239000000701 coagulant Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- -1 vinylbenzyl Chemical group 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24029884A JPS61118406A (ja) | 1984-11-14 | 1984-11-14 | 水溶性ポリビニルアミンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24029884A JPS61118406A (ja) | 1984-11-14 | 1984-11-14 | 水溶性ポリビニルアミンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61118406A true JPS61118406A (ja) | 1986-06-05 |
| JPH0535163B2 JPH0535163B2 (enrdf_load_stackoverflow) | 1993-05-25 |
Family
ID=17057385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24029884A Granted JPS61118406A (ja) | 1984-11-14 | 1984-11-14 | 水溶性ポリビニルアミンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61118406A (enrdf_load_stackoverflow) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS636198A (ja) * | 1986-06-20 | 1988-01-12 | 三菱化学株式会社 | 紙の製法 |
| DE3909004A1 (de) * | 1989-03-18 | 1990-09-27 | Basf Ag | Verwendung von nicht hydrolysierten n-vinylformamid-einheiten enthaltenden copolymerisaten bei der papierherstellung |
| WO1990011253A1 (de) * | 1989-03-18 | 1990-10-04 | Basf Aktiengesellschaft | Verwendung von nicht hydrolysierten n-vinylformamid-einheiten enthaltenden copolymerisaten als flockungs- und entwässerungsmittel |
| US5119532A (en) * | 1990-03-30 | 1992-06-09 | Kabushiki Kaisha Toka-Rida-Denki-Seisakusho | Buckle apparatus |
| US5324792A (en) * | 1993-03-25 | 1994-06-28 | Air Products And Chemicals, Inc. | Process for making amidine-containing polymers |
| US5391710A (en) * | 1993-03-25 | 1995-02-21 | Air Products And Chemicals, Inc. | Production of amine functional polymers having improved purity |
| US5436299A (en) * | 1994-12-20 | 1995-07-25 | Air Products And Chemicals, Inc. | Decarbonylation of N-vinylformamide copolymers |
| US5491199A (en) * | 1995-02-22 | 1996-02-13 | Air Products And Chemicals, Inc. | One step production of low salt vinylamine polymers |
| US5681912A (en) * | 1993-11-12 | 1997-10-28 | Betzdearborn Inc. | Water-soluble cationic copolymers and their use as flocculants and drainage retention aids |
| JPH11315116A (ja) * | 1998-03-09 | 1999-11-16 | Natl Starch & Chem Investment Holding Corp | Ｎ―ビニルホルムアミドモノマ―からポリマ―を製造する方法 |
| WO2003102036A1 (fr) * | 2002-05-31 | 2003-12-11 | Mitsubishi Chemical Corporation | Copolymere a fonctionnalite amine et procede de production de ce copolymere |
| WO2010023799A1 (ja) | 2008-09-01 | 2010-03-04 | ダイヤニトリックス株式会社 | Ｎ－ビニルカルボン酸アミド系重合体の製造方法 |
| WO2010030372A2 (en) | 2008-09-12 | 2010-03-18 | Sekisui Specialty Chemicals America Llc | Improved nvf copolymer process |
| WO2015068806A1 (ja) | 2013-11-08 | 2015-05-14 | 三菱レイヨン株式会社 | ビニルアミン（共）重合体の製造方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6811839B2 (en) | 2000-11-09 | 2004-11-02 | Canon Kabushiki Kaisha | Recording medium and image forming process using the same |
| JP2009034942A (ja) | 2007-08-03 | 2009-02-19 | Fujifilm Corp | インクジェット記録用媒体 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5823809A (ja) * | 1981-07-18 | 1983-02-12 | バスフ・アクチエンゲゼルシヤフト | 線状塩基性重合物、その製法及び使用 |
-
1984
- 1984-11-14 JP JP24029884A patent/JPS61118406A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5823809A (ja) * | 1981-07-18 | 1983-02-12 | バスフ・アクチエンゲゼルシヤフト | 線状塩基性重合物、その製法及び使用 |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS636198A (ja) * | 1986-06-20 | 1988-01-12 | 三菱化学株式会社 | 紙の製法 |
| DE3909004A1 (de) * | 1989-03-18 | 1990-09-27 | Basf Ag | Verwendung von nicht hydrolysierten n-vinylformamid-einheiten enthaltenden copolymerisaten bei der papierherstellung |
| WO1990011253A1 (de) * | 1989-03-18 | 1990-10-04 | Basf Aktiengesellschaft | Verwendung von nicht hydrolysierten n-vinylformamid-einheiten enthaltenden copolymerisaten als flockungs- und entwässerungsmittel |
| US5225088A (en) * | 1989-03-18 | 1993-07-06 | Basf Aktiengesellschaft | Use of nonhydrolyzed copolymers containing n-vinylformamide units as flocculants and drainage aids |
| US5119532A (en) * | 1990-03-30 | 1992-06-09 | Kabushiki Kaisha Toka-Rida-Denki-Seisakusho | Buckle apparatus |
| US5324792A (en) * | 1993-03-25 | 1994-06-28 | Air Products And Chemicals, Inc. | Process for making amidine-containing polymers |
| US5367035A (en) * | 1993-03-25 | 1994-11-22 | Air Products And Chemicals, Inc. | Poly(vinylammonium formate) and process for making the same |
| US5391710A (en) * | 1993-03-25 | 1995-02-21 | Air Products And Chemicals, Inc. | Production of amine functional polymers having improved purity |
| US5393842A (en) * | 1993-03-25 | 1995-02-28 | Air Products And Chemicals, Inc. | Poly(vinylammonium formate) |
| US5401808A (en) * | 1993-03-25 | 1995-03-28 | Air Products And Chemicals, Inc. | Poly(vinylammonium formate) and process for making amidine-containing polymers |
| US5681912A (en) * | 1993-11-12 | 1997-10-28 | Betzdearborn Inc. | Water-soluble cationic copolymers and their use as flocculants and drainage retention aids |
| US5436299A (en) * | 1994-12-20 | 1995-07-25 | Air Products And Chemicals, Inc. | Decarbonylation of N-vinylformamide copolymers |
| DE19606440A1 (de) * | 1995-02-22 | 1996-08-29 | Air Prod & Chem | Einstufiges Verfahren zur Herstellung von Vinylamin-Polymeren mit geringem Salzgehalt |
| US5491199A (en) * | 1995-02-22 | 1996-02-13 | Air Products And Chemicals, Inc. | One step production of low salt vinylamine polymers |
| DE19606440C2 (de) * | 1995-02-22 | 2002-10-17 | Univ Pittsburgh Pittsburgh | Einstufiges Verfahren zur Herstellung von Vinylamin-Polymeren mit geringem Salzgehalt |
| JPH11315116A (ja) * | 1998-03-09 | 1999-11-16 | Natl Starch & Chem Investment Holding Corp | Ｎ―ビニルホルムアミドモノマ―からポリマ―を製造する方法 |
| WO2003102036A1 (fr) * | 2002-05-31 | 2003-12-11 | Mitsubishi Chemical Corporation | Copolymere a fonctionnalite amine et procede de production de ce copolymere |
| WO2010023799A1 (ja) | 2008-09-01 | 2010-03-04 | ダイヤニトリックス株式会社 | Ｎ－ビニルカルボン酸アミド系重合体の製造方法 |
| WO2010030372A2 (en) | 2008-09-12 | 2010-03-18 | Sekisui Specialty Chemicals America Llc | Improved nvf copolymer process |
| WO2015068806A1 (ja) | 2013-11-08 | 2015-05-14 | 三菱レイヨン株式会社 | ビニルアミン（共）重合体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0535163B2 (enrdf_load_stackoverflow) | 1993-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |