GB812983A - New polymerisable ester and polymers obtained therefrom - Google Patents
New polymerisable ester and polymers obtained therefromInfo
- Publication number
- GB812983A GB812983A GB1855056A GB1855056A GB812983A GB 812983 A GB812983 A GB 812983A GB 1855056 A GB1855056 A GB 1855056A GB 1855056 A GB1855056 A GB 1855056A GB 812983 A GB812983 A GB 812983A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- dimethyl vinylphosphonate
- polymerized
- vinylphosphonate
- copolymerized
- 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
Links
- 150000002148 esters Chemical class 0.000 title 1
- 229920000642 polymer Polymers 0.000 title 1
- CQCXMYUCNSJSKG-UHFFFAOYSA-N 1-dimethoxyphosphorylethene Chemical compound COP(=O)(OC)C=C CQCXMYUCNSJSKG-UHFFFAOYSA-N 0.000 abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 abstract 2
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 abstract 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 abstract 1
- JCXIVFAMGPGRGX-UHFFFAOYSA-N 1-bromo-2-dimethoxyphosphorylethane Chemical compound COP(=O)(OC)CCBr JCXIVFAMGPGRGX-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001169 thermoplastic Polymers 0.000 abstract 1
- 239000004416 thermosoftening plastic Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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 and 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 and 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Dimethyl vinylphosphonate is polymerized in the presence of a non-peroxide catalyst, e.g. azo diisobutyronitrile, to a colourless watersoluble thermoplastic glass-like material. It may also be copolymerized with other polymerizable compounds, e.g. acrylic or methacrylic esters. In examples, dimethyl vinylphosphonate is polymerized alone and with methyl methacrylate in the presence of azodiisobutyronitrile. Specification 796,838 is referred to.ALSO:The invention comprises dimethyl vinylphosphonate and its preparation by reacting trimethyl phosphite with 1,2-dihaloethane and dehydrohalogenating the product with a base. Suitable haloethanes are 1,2-dichloro-, 1,2-dibromo- and 1-chloro-2-bromo-ethane. In an example, trimethyl phosphite (prepared from PCl3 and methanol in the presence of diethylaniline in petroleum ether) is refluxed with 1,2-dibromoethane to form dimethyl 2-bromoethylphosphonate, which is reacted with triethylamine in benzene to form the dimethyl vinylphosphonate. The dimethyl vinylphosphonate may be polymerized or copolymerized (see Group IV (a)). Specification 796,838 is referred to.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI13348A DE1079325B (en) | 1956-06-15 | 1957-06-13 | Process for the preparation of non-flammable resinous polymers and copolymers containing esters of phosphoric oxygen acids |
| FR1179432D FR1179432A (en) | 1956-06-15 | 1957-06-15 | Dimethyl vinylphosphonate and its polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB812983A true GB812983A (en) | 1959-05-06 |
Family
ID=1734009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1855056A Expired GB812983A (en) | 1956-06-15 | 1956-06-15 | New polymerisable ester and polymers obtained therefrom |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB812983A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297663A (en) * | 1959-11-11 | 1967-01-10 | Hoechst Ag | Vinylphosphonic acid polymers and process for making them |
| CN106459272A (en) * | 2014-06-03 | 2017-02-22 | 丸善石油化学株式会社 | Method for producing dimethyl polyvinylphosphonate and polyvinylphosphonic acid |
-
1956
- 1956-06-15 GB GB1855056A patent/GB812983A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297663A (en) * | 1959-11-11 | 1967-01-10 | Hoechst Ag | Vinylphosphonic acid polymers and process for making them |
| CN106459272A (en) * | 2014-06-03 | 2017-02-22 | 丸善石油化学株式会社 | Method for producing dimethyl polyvinylphosphonate and polyvinylphosphonic acid |
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