CA2736873C - Improved nvf copolymer process - Google Patents
Improved nvf copolymer process Download PDFInfo
- Publication number
- CA2736873C CA2736873C CA2736873A CA2736873A CA2736873C CA 2736873 C CA2736873 C CA 2736873C CA 2736873 A CA2736873 A CA 2736873A CA 2736873 A CA2736873 A CA 2736873A CA 2736873 C CA2736873 C CA 2736873C
- Authority
- CA
- Canada
- Prior art keywords
- mol
- vinyl
- equal
- copolymer
- water
- 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 - Fee Related
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 167
- 238000000034 method Methods 0.000 title claims abstract description 43
- 230000008569 process Effects 0.000 title claims abstract description 28
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 94
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims abstract description 82
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 18
- 238000010828 elution Methods 0.000 claims abstract description 17
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 57
- 230000007062 hydrolysis Effects 0.000 claims description 26
- 238000006460 hydrolysis reaction Methods 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 150000001409 amidines Chemical group 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 17
- 239000002685 polymerization catalyst Substances 0.000 claims description 16
- 238000010526 radical polymerization reaction Methods 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 12
- 241001550224 Apha Species 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical group NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 7
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 claims description 5
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 abstract description 36
- 238000009826 distribution Methods 0.000 abstract description 18
- 239000000178 monomer Substances 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- -1 vinyl amine Chemical class 0.000 description 28
- 239000003999 initiator Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 150000001412 amines Chemical group 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- 230000035484 reaction time Effects 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 229920005604 random copolymer Polymers 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001408 amides Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- 229920003169 water-soluble polymer Polymers 0.000 description 4
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 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 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229920006322 acrylamide copolymer Polymers 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- OZFIGURLAJSLIR-UHFFFAOYSA-N 1-ethenyl-2h-pyridine Chemical compound C=CN1CC=CC=C1 OZFIGURLAJSLIR-UHFFFAOYSA-N 0.000 description 1
- 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
- DXLZNKULUVFFFY-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate;hydrochloride Chemical compound Cl.NCCOC(=O)C=C DXLZNKULUVFFFY-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- QJPVLBSIXNKVDY-UHFFFAOYSA-N methylamino 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)ONC QJPVLBSIXNKVDY-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical class [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- AUIQILSKFKITRO-UHFFFAOYSA-N styrene;trimethylazanium;chloride Chemical compound [Cl-].C[NH+](C)C.C=CC1=CC=CC=C1 AUIQILSKFKITRO-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000003039 volatile agent 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
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9675608P | 2008-09-12 | 2008-09-12 | |
| US61/096,756 | 2008-09-12 | ||
| PCT/US2009/005098 WO2010030372A2 (en) | 2008-09-12 | 2009-09-11 | Improved nvf copolymer process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2736873A1 CA2736873A1 (en) | 2010-03-18 |
| CA2736873C true CA2736873C (en) | 2014-04-08 |
Family
ID=41650145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2736873A Expired - Fee Related CA2736873C (en) | 2008-09-12 | 2009-09-11 | Improved nvf copolymer process |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20110160418A1 (enExample) |
| EP (1) | EP2326675A2 (enExample) |
| JP (3) | JP2012502164A (enExample) |
| CN (2) | CN102149734A (enExample) |
| CA (1) | CA2736873C (enExample) |
| WO (1) | WO2010030372A2 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102206300B (zh) * | 2011-04-08 | 2012-08-08 | 南京大学 | 一种共聚物的制备方法、由该制备方法得到的共聚物及其在水处理中的应用 |
| JP6584633B2 (ja) * | 2015-07-24 | 2019-10-02 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 連続した反応器ユニットにおけるｎ−ビニルカルボキサミドの製造 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4255548A (en) | 1980-01-07 | 1981-03-10 | Dynapol | Ethylene-vinylamine copolymers |
| DE3128478A1 (de) * | 1981-07-18 | 1983-02-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von linearen, basischen polymerisaten |
| US4393174A (en) | 1981-11-09 | 1983-07-12 | Dynapol | Base hydrolysis of pendant amide polymers |
| JPS61118406A (ja) | 1984-11-14 | 1986-06-05 | Mitsubishi Chem Ind Ltd | 水溶性ポリビニルアミンの製造方法 |
| DE3534273A1 (de) * | 1985-09-26 | 1987-04-02 | Basf Ag | Verfahren zur herstellung von vinylamin-einheiten enthaltenden wasserloeslichen copolymerisaten und deren verwendung als nass- und trockenverfestigungsmittel fuer papier |
| US4808683A (en) * | 1986-06-19 | 1989-02-28 | Mitsubishi Chemical Industries Limited | Vinylamine copolymer, flocculating agent using the same, and process for preparing the same |
| CA1283748C (en) | 1986-06-25 | 1991-04-30 | Takaharu Itagaki | Vinylamine copolymer, flocculating agent and paper strength increasingagent using the same, as well as process for producing the same |
| JPH0676462B2 (ja) * | 1986-06-30 | 1994-09-28 | 三菱化成株式会社 | ビニルアミン共重合体およびその製法 |
| US4921621A (en) | 1986-10-01 | 1990-05-01 | Air Products And Chemicals, Inc. | Hydrolyzed co-polymers of N-vinylamide and acrylamide for use as waterloss control additives in drilling mud |
| US5300566A (en) * | 1988-04-15 | 1994-04-05 | Air Products And Chemicals, Inc. | Method for preparing poly(vinyl alcohol)-co-poly(vinylamine) via a two-phase process |
| CA1330684C (en) * | 1988-04-15 | 1994-07-12 | Robert Krantz Pinschmidt Jr. | Method for preparing poly(vinyl alcohol)- co-poly(vinylamine) via a two-phase process |
| US4943676A (en) | 1989-07-12 | 1990-07-24 | Air Products And Chemicals, Inc. | Thermolysis of poly(N-vinylformamide) to poly(N-vinylamine) |
| DE69210914T2 (de) | 1991-08-20 | 1997-01-16 | Mitsubishi Chem Corp | Kationisches polymeres Flockungsmittel |
| US5491199A (en) * | 1995-02-22 | 1996-02-13 | Air Products And Chemicals, Inc. | One step production of low salt vinylamine polymers |
| JP3926054B2 (ja) * | 1999-02-01 | 2007-06-06 | 三菱化学株式会社 | Ｎ−ビニルアミド−酢酸ビニル系共重合体加水分解物の製造方法 |
| US6559227B1 (en) * | 2000-07-28 | 2003-05-06 | Mitsubishi Chemical Corporation | Process for producing vinylamine-vinyl alcohol copolymer and use of the copolymer |
| JP4531240B2 (ja) * | 2000-11-09 | 2010-08-25 | 日本合成化学工業株式会社 | ビニルアルコール−ビニルアミン共重合体の製造法 |
| CN1307209C (zh) * | 2001-12-21 | 2007-03-28 | 西巴特殊化学品控股有限公司 | 包括官能团部分的聚(乙烯醇)－共－聚(乙烯胺)聚合物 |
| EP1458769B1 (en) * | 2001-12-21 | 2008-12-31 | Ciba Holding Inc. | Poly(vinyl alcohol)-co-poly(n-vinyl formamide) copolymers |
-
2009
- 2009-09-11 CN CN2009801354778A patent/CN102149734A/zh active Pending
- 2009-09-11 CN CN201610099291.3A patent/CN105524205A/zh active Pending
- 2009-09-11 EP EP09796143A patent/EP2326675A2/en not_active Withdrawn
- 2009-09-11 JP JP2011526862A patent/JP2012502164A/ja not_active Ceased
- 2009-09-11 US US12/998,026 patent/US20110160418A1/en not_active Abandoned
- 2009-09-11 CA CA2736873A patent/CA2736873C/en not_active Expired - Fee Related
- 2009-09-11 WO PCT/US2009/005098 patent/WO2010030372A2/en not_active Ceased
-
2015
- 2015-03-25 JP JP2015062724A patent/JP2015134933A/ja not_active Ceased
-
2016
- 2016-09-16 JP JP2016181856A patent/JP2017025331A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010030372A2 (en) | 2010-03-18 |
| CA2736873A1 (en) | 2010-03-18 |
| CN102149734A (zh) | 2011-08-10 |
| JP2015134933A (ja) | 2015-07-27 |
| WO2010030372A3 (en) | 2010-05-06 |
| EP2326675A2 (en) | 2011-06-01 |
| CN105524205A (zh) | 2016-04-27 |
| US20110160418A1 (en) | 2011-06-30 |
| JP2012502164A (ja) | 2012-01-26 |
| JP2017025331A (ja) | 2017-02-02 |
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