DE1106963B - Verfahren zur Herstellung von Polyvinylphosphonsaeure - Google Patents
Verfahren zur Herstellung von PolyvinylphosphonsaeureInfo
- Publication number
- DE1106963B DE1106963B DEF29824A DEF0029824A DE1106963B DE 1106963 B DE1106963 B DE 1106963B DE F29824 A DEF29824 A DE F29824A DE F0029824 A DEF0029824 A DE F0029824A DE 1106963 B DE1106963 B DE 1106963B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- acid
- hours
- ethyl acetate
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 claims description 3
- 229960004592 isopropanol Drugs 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- -1 Toluyl peroxide Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JMYZLRSSLFFUQN-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1Cl JMYZLRSSLFFUQN-UHFFFAOYSA-N 0.000 description 1
- MLSZIADXWDYFKM-UHFFFAOYSA-N 1-dichlorophosphorylethene Chemical compound ClP(Cl)(=O)C=C MLSZIADXWDYFKM-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- VMOJXADNUCNCRK-UHFFFAOYSA-N 3-methylbutane-1-sulfinic acid Chemical compound CC(C)CCS(O)=O VMOJXADNUCNCRK-UHFFFAOYSA-N 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16K—VALVES; TAPS; COCKS; ACTUATING-FLOATS; DEVICES FOR VENTING OR AERATING
- F16K1/00—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces
- F16K1/16—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members
- F16K1/18—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps
- F16K1/22—Lift valves or globe valves, i.e. cut-off apparatus with closure members having at least a component of their opening and closing motion perpendicular to the closing faces with pivoted closure-members with pivoted discs or flaps with axis of rotation crossing the valve member, e.g. butterfly valves
- F16K1/222—Shaping of the valve member
-
- 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
- C08F30/00—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29824A DE1106963B (de) | 1959-11-11 | 1959-11-11 | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
| DEF30249A DE1135176B (de) | 1959-11-11 | 1960-01-08 | Verfahren zur Herstellung phosphorhaltiger Mischpolymerisate |
| CH1246860A CH412335A (de) | 1959-11-11 | 1960-11-08 | Verfahren zur Herstellung von phosphorhaltigen Polymerisaten |
| NL257817A NL112731C (en, 2012) | 1959-11-11 | 1960-11-10 | |
| FR843705A FR1274011A (fr) | 1959-11-11 | 1960-11-10 | Polymères de l'acide vinylphosphonique et leur procédé de préparation |
| GB38870/60A GB933107A (en) | 1959-11-11 | 1960-11-11 | Vinylphosphonic acid polymers and process for making them |
| BE597048A BE597048A (fr) | 1959-11-11 | 1960-11-14 | Polymères de l'acide vinylphosphonique et leur procédé de préparation |
| US405870A US3297663A (en) | 1959-11-11 | 1964-10-22 | Vinylphosphonic acid polymers and process for making them |
| NL6512896A NL6512896A (en, 2012) | 1959-11-11 | 1965-10-05 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29824A DE1106963B (de) | 1959-11-11 | 1959-11-11 | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
| DEF30249A DE1135176B (de) | 1959-11-11 | 1960-01-08 | Verfahren zur Herstellung phosphorhaltiger Mischpolymerisate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1106963B true DE1106963B (de) | 1961-05-18 |
Family
ID=39246461
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF29824A Pending DE1106963B (de) | 1959-11-11 | 1959-11-11 | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
| DEF30249A Pending DE1135176B (de) | 1959-11-11 | 1960-01-08 | Verfahren zur Herstellung phosphorhaltiger Mischpolymerisate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30249A Pending DE1135176B (de) | 1959-11-11 | 1960-01-08 | Verfahren zur Herstellung phosphorhaltiger Mischpolymerisate |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3297663A (en, 2012) |
| BE (1) | BE597048A (en, 2012) |
| CH (1) | CH412335A (en, 2012) |
| DE (2) | DE1106963B (en, 2012) |
| FR (1) | FR1274011A (en, 2012) |
| GB (1) | GB933107A (en, 2012) |
| NL (2) | NL112731C (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446028A (en) * | 1982-12-20 | 1984-05-01 | Betz Laboratories, Inc. | Isopropenyl phosphonic acid copolymers used to inhibit scale formation |
| US4446046A (en) * | 1981-06-17 | 1984-05-01 | Betz Laboratories, Inc. | Poly (alkenyl) phosphonic acid and methods of use thereof |
| EP0114394A3 (en) * | 1982-12-29 | 1985-12-04 | Hoechst Aktiengesellschaft | Process for preparing polymers of vinyl phosphonic acid in solvents |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106963B (de) * | 1959-11-11 | 1961-05-18 | Hoechst Ag | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
| DE1570574C3 (de) * | 1965-05-24 | 1973-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Phos phor enthaltenden Polymerisaten oder Mischpolymerisaten |
| DE1569993A1 (de) * | 1965-10-29 | 1969-08-28 | Hoechst Ag | Verwendung einer Mischung aus Vinylester/Vinylphosphonsaeureester-Copolymerisaten und Naturharzen und bzw.oder Kunstharzen als Haftkleber |
| US3943074A (en) * | 1973-06-08 | 1976-03-09 | S.A. Texaco Belgium N.V. | Vinyl phosphonic acid-divinyl sulfone copolymer ion exchange resin |
| JPS53134037A (en) * | 1977-04-27 | 1978-11-22 | Kuraray Co Ltd | Adhesive for human hard tissue with good adhesiveness |
| US4342857A (en) * | 1980-12-31 | 1982-08-03 | Colgate-Palmolive Company | Antigingivitis composition comprising vinyl phosphonic acid/vinyl phosphonyl fluoride copolymer |
| DE3126627A1 (de) * | 1981-07-06 | 1983-01-20 | Hoechst Ag, 6000 Frankfurt | Polyvinylmethylphosphinsaeure, verfahren zu ihrer herstellung und ihre verwendung |
| DE3379330D1 (en) * | 1982-12-09 | 1989-04-13 | Cassella Farbwerke Mainkur Ag | Water soluble polymers, their preparation and their use |
| DE3248019A1 (de) * | 1982-12-24 | 1984-06-28 | Cassella Ag, 6000 Frankfurt | Wasserloesliche copolymerisate, ihre herstellung und ihre verwendung |
| DE3314569A1 (de) * | 1983-04-22 | 1984-10-25 | Cassella Ag, 6000 Frankfurt | Vernetzte hydrophile copolymerisate, ihre herstellung und verwendung |
| DE3418496A1 (de) * | 1984-05-18 | 1985-11-21 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von mischpolymerisaten aus vinylphosphonsaeure und (meth-)acrylsaeure in waessriger loesung und ihre verwendung |
| US4822861A (en) * | 1988-03-15 | 1989-04-18 | Polychrome Corporation | Method for the preparation of polyvinyl phosphonic acid |
| DE3817424A1 (de) * | 1988-05-21 | 1989-11-23 | Hoechst Ag | Alkenylphosphon- und -phosphinsaeureester, verfahren zu ihrer herstellung und durch strahlung polymerisierbares gemisch, das diese verbindungen enthaelt |
| DE3922330A1 (de) * | 1989-07-07 | 1991-01-17 | Hoechst Ag | Durch strahlung polymerisierbares gemisch und dieses enthaltendes aufzeichnungsmaterial |
| BE1003944A3 (fr) * | 1990-10-02 | 1992-07-22 | Interox Sa | Polymeres organophosphoniques et leur utilisation comme stabilisants de solutions aqueuses de peroxyde d'hydrogene. |
| GB9102501D0 (en) * | 1991-02-06 | 1991-03-27 | Nat Res Dev | Synthesis of poly(vinyl phosphonic acid) |
| US5281631A (en) * | 1991-12-20 | 1994-01-25 | Arch Development Corp. | Phosphonic acid based ion exchange resins |
| US5241028A (en) * | 1992-05-29 | 1993-08-31 | The Dow Chemical Company | Polymerizing ethylene-ionic comonomer using inverse micellar process |
| KR100564430B1 (ko) * | 2003-07-16 | 2006-03-28 | 주식회사 하이닉스반도체 | 유기 반사 방지막 중합체, 이의 제조 방법 및 이를함유하는 반사 방지막 조성물 |
| US8076432B2 (en) * | 2004-07-07 | 2011-12-13 | Unichem Technologies, Inc. | Phosphonic compounds and methods of use thereof |
| WO2008090152A1 (de) * | 2007-01-22 | 2008-07-31 | Basf Se | Verfahren zur herstellung von copolymeren der vinylphosphonsäure |
| JP7075583B2 (ja) * | 2018-03-26 | 2022-05-26 | 国立大学法人福井大学 | ポリビニルホスホン酸の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2784169A (en) * | 1954-06-14 | 1957-03-05 | Monsanto Chemicals | Acrylonitrile polymers stabilized with salts of vinyl phosphonates |
| DE1020019B (de) * | 1956-03-14 | 1957-11-28 | Hoechst Ag | Verfahren zur Herstellung von Vinylphosphonsaeuredichlorid |
| GB812983A (en) * | 1956-06-15 | 1959-05-06 | Ici Ltd | New polymerisable ester and polymers obtained therefrom |
| DE1032537B (de) * | 1956-09-21 | 1958-06-19 | Hoechst Ag | Verfahren zur Herstellung von phosphorhaltigen Polymerisaten |
| GB853008A (en) * | 1958-06-20 | 1960-11-02 | Ici Ltd | Polymers containing phosphorus |
| DE1106963B (de) * | 1959-11-11 | 1961-05-18 | Hoechst Ag | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
-
1959
- 1959-11-11 DE DEF29824A patent/DE1106963B/de active Pending
-
1960
- 1960-01-08 DE DEF30249A patent/DE1135176B/de active Pending
- 1960-11-08 CH CH1246860A patent/CH412335A/de unknown
- 1960-11-10 FR FR843705A patent/FR1274011A/fr not_active Expired
- 1960-11-10 NL NL257817A patent/NL112731C/xx active
- 1960-11-11 GB GB38870/60A patent/GB933107A/en not_active Expired
- 1960-11-14 BE BE597048A patent/BE597048A/fr unknown
-
1964
- 1964-10-22 US US405870A patent/US3297663A/en not_active Expired - Lifetime
-
1965
- 1965-10-05 NL NL6512896A patent/NL6512896A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446046A (en) * | 1981-06-17 | 1984-05-01 | Betz Laboratories, Inc. | Poly (alkenyl) phosphonic acid and methods of use thereof |
| US4446028A (en) * | 1982-12-20 | 1984-05-01 | Betz Laboratories, Inc. | Isopropenyl phosphonic acid copolymers used to inhibit scale formation |
| EP0114394A3 (en) * | 1982-12-29 | 1985-12-04 | Hoechst Aktiengesellschaft | Process for preparing polymers of vinyl phosphonic acid in solvents |
Also Published As
| Publication number | Publication date |
|---|---|
| GB933107A (en) | 1963-08-08 |
| FR1274011A (fr) | 1961-10-20 |
| BE597048A (fr) | 1961-05-15 |
| NL112731C (en, 2012) | 1966-04-15 |
| DE1135176B (de) | 1962-08-23 |
| CH412335A (de) | 1966-04-30 |
| NL257817A (en, 2012) | 1965-11-15 |
| US3297663A (en) | 1967-01-10 |
| NL6512896A (en, 2012) | 1965-12-27 |
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