DE69212657T2 - Synthese von Vinylphosphonsäure - Google Patents
Synthese von VinylphosphonsäureInfo
- Publication number
- DE69212657T2 DE69212657T2 DE69212657T DE69212657T DE69212657T2 DE 69212657 T2 DE69212657 T2 DE 69212657T2 DE 69212657 T DE69212657 T DE 69212657T DE 69212657 T DE69212657 T DE 69212657T DE 69212657 T2 DE69212657 T2 DE 69212657T2
- Authority
- DE
- Germany
- Prior art keywords
- crosslinker
- process according
- bonded
- polymerization
- vinylphosphonyl
- 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
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- -1 poly(vinylphosphonic acid) Polymers 0.000 claims description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- 150000004770 chalcogenides Chemical class 0.000 claims description 4
- 239000003178 glass ionomer cement Substances 0.000 claims description 4
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical group C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 239000004568 cement Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YDONNITUKPKTIG-UHFFFAOYSA-N [Nitrilotris(methylene)]trisphosphonic acid Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CP(O)(O)=O YDONNITUKPKTIG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 239000005354 aluminosilicate glass Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 238000009960 carding Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229910001610 cryolite Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B28/00—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements
- C04B28/28—Compositions of mortars, concrete or artificial stone, containing inorganic binders or the reaction product of an inorganic and an organic binder, e.g. polycarboxylate cements containing organic polyacids, e.g. polycarboxylate cements, i.e. ionomeric systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ceramic Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919102501A GB9102501D0 (en) | 1991-02-06 | 1991-02-06 | Synthesis of poly(vinyl phosphonic acid) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69212657D1 DE69212657D1 (de) | 1996-09-19 |
| DE69212657T2 true DE69212657T2 (de) | 1997-01-02 |
Family
ID=10689601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69212657T Expired - Fee Related DE69212657T2 (de) | 1991-02-06 | 1992-01-29 | Synthese von Vinylphosphonsäure |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5278266A (enExample) |
| EP (1) | EP0498560B1 (enExample) |
| JP (1) | JPH0578421A (enExample) |
| DE (1) | DE69212657T2 (enExample) |
| GB (2) | GB9102501D0 (enExample) |
| IN (1) | IN185009B (enExample) |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106963B (de) * | 1959-11-11 | 1961-05-18 | Hoechst Ag | Verfahren zur Herstellung von Polyvinylphosphonsaeure |
| US3576793A (en) * | 1967-05-08 | 1971-04-27 | Monsanto Co | Polymers of alkylene diphosphonic acids and salts and copolymers thereof |
| US3943074A (en) * | 1973-06-08 | 1976-03-09 | S.A. Texaco Belgium N.V. | Vinyl phosphonic acid-divinyl sulfone copolymer ion exchange resin |
| US4342857A (en) * | 1980-12-31 | 1982-08-03 | Colgate-Palmolive Company | Antigingivitis composition comprising vinyl phosphonic acid/vinyl phosphonyl fluoride copolymer |
| DE3248491A1 (de) * | 1982-12-29 | 1984-07-05 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von polymerisaten der vinylphosphonsaeure in protischen loesungsmitteln |
| JPS59135272A (ja) * | 1983-01-21 | 1984-08-03 | Kuraray Co Ltd | 接着剤 |
| US5077366A (en) * | 1987-08-07 | 1991-12-31 | The Dow Chemical Company | Novel phosphonic acid compounds and method of preparation |
| US4822861A (en) * | 1988-03-15 | 1989-04-18 | Polychrome Corporation | Method for the preparation of polyvinyl phosphonic acid |
| GB8809998D0 (en) * | 1988-04-27 | 1988-06-02 | Wilson A D | Poly-vinylphosphonic acid & metal oxide/cement/glass ionomer cement |
-
1991
- 1991-02-06 GB GB919102501A patent/GB9102501D0/en active Pending
-
1992
- 1992-01-29 EP EP92300747A patent/EP0498560B1/en not_active Expired - Lifetime
- 1992-01-29 DE DE69212657T patent/DE69212657T2/de not_active Expired - Fee Related
- 1992-01-29 GB GB9201847A patent/GB2252560B/en not_active Expired - Fee Related
- 1992-02-03 IN IN76DE1992 patent/IN185009B/en unknown
- 1992-02-05 US US07/831,578 patent/US5278266A/en not_active Expired - Fee Related
- 1992-02-06 JP JP4021029A patent/JPH0578421A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2252560A (en) | 1992-08-12 |
| GB9102501D0 (en) | 1991-03-27 |
| GB9201847D0 (en) | 1992-03-18 |
| IN185009B (enExample) | 2000-10-21 |
| GB2252560B (en) | 1994-10-19 |
| EP0498560A1 (en) | 1992-08-12 |
| US5278266A (en) | 1994-01-11 |
| JPH0578421A (ja) | 1993-03-30 |
| EP0498560B1 (en) | 1996-08-14 |
| DE69212657D1 (de) | 1996-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: BTG INTERNATIONAL LTD., LONDON, GB |
|
| 8339 | Ceased/non-payment of the annual fee |