GB1111796A - 1-cyanovinyl alkyl carbonates,process for their production and polymers thereof - Google Patents
1-cyanovinyl alkyl carbonates,process for their production and polymers thereofInfo
- Publication number
- GB1111796A GB1111796A GB314767A GB314767A GB1111796A GB 1111796 A GB1111796 A GB 1111796A GB 314767 A GB314767 A GB 314767A GB 314767 A GB314767 A GB 314767A GB 1111796 A GB1111796 A GB 1111796A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- cyanovinyl
- esters
- formula
- polymers
- 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
- 229920000642 polymer Polymers 0.000 title abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- IHACYHISAXGZGX-UHFFFAOYSA-N 1-cyanoethenyl ethyl carbonate Chemical compound CCOC(=O)OC(=C)C#N IHACYHISAXGZGX-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- MOOSTLKPWVLQSI-UHFFFAOYSA-N 2-chloro-2-hydroxypropanenitrile Chemical compound ClC(C#N)(O)C MOOSTLKPWVLQSI-UHFFFAOYSA-N 0.000 abstract 1
- IUPVIQCDWOEEIN-UHFFFAOYSA-N 2-cyanoethenyl hydrogen carbonate Chemical class OC(=O)OC=CC#N IUPVIQCDWOEEIN-UHFFFAOYSA-N 0.000 abstract 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- 125000005395 methacrylic acid group Chemical class 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Cyanovinyl carbonates of the formula <FORM:1111796/C3/1> wherein R is a C1- 20 alkyl (including cycloalky and aralkyl) group, may be homopolymerized, or copolymerized with another compound of the above formula or with a different monoethylenically unsaturated polymerizable monomer. In examples 1-cyano-vinyl ethyl carbonate is polymerized in bulk in the presence of benzoyl peroxide under nitrogen, and copolymerized with styrene under similar conditions. Other suitable polymerization catalysts include persulphates, e.g. potassium persulphate. Other comonomers specified are vinyl esters, vinylidene chloride, acrylic and methacrylic acids and their esters, nitriles and amides, substituted styrenes, esters and amides of fumaric, citraconic and maleic acids, and olefins. The polymers can be moulded into articles such as blocks, sheets and films.ALSO:Compounds of the formula <FORM:1111796/C2/1> wherein R is a C1-20 alkyl (including cycloalkyl and aralkyl) group may be obtained by reacting an alkyl haloformate with 2-chlorolactonitrile in the presence of an alkaline reagent to form the 2-chloro-1-cyanoethyl alkyl carbonate and then dehydrochlorinating the later by reaction with a tertiary amine thus forming the 1-cyanovinyl alkyl carbonate. The products may be stabilized with a phenolic stabilizer, e.g. t-butyl catechol, and they are stated to possess anthelmintic properties.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB314767A GB1111796A (en) | 1967-01-20 | 1967-01-20 | 1-cyanovinyl alkyl carbonates,process for their production and polymers thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB314767A GB1111796A (en) | 1967-01-20 | 1967-01-20 | 1-cyanovinyl alkyl carbonates,process for their production and polymers thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111796A true GB1111796A (en) | 1968-05-01 |
Family
ID=9752836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB314767A Expired GB1111796A (en) | 1967-01-20 | 1967-01-20 | 1-cyanovinyl alkyl carbonates,process for their production and polymers thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1111796A (en) |
-
1967
- 1967-01-20 GB GB314767A patent/GB1111796A/en not_active Expired
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