GB1116005A - Vinyl n-heterocyclic carbamates, process for their production and polymers thereof - Google Patents
Vinyl n-heterocyclic carbamates, process for their production and polymers thereofInfo
- Publication number
- GB1116005A GB1116005A GB741166A GB741166A GB1116005A GB 1116005 A GB1116005 A GB 1116005A GB 741166 A GB741166 A GB 741166A GB 741166 A GB741166 A GB 741166A GB 1116005 A GB1116005 A GB 1116005A
- Authority
- GB
- United Kingdom
- Prior art keywords
- vinyl
- carbamates
- heterocyclic
- secondary amine
- aziridinyl
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title abstract 5
- 229920002554 vinyl polymer Polymers 0.000 title abstract 4
- 229920000642 polymer Polymers 0.000 title 1
- -1 ethylene, propylene Chemical class 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000003335 secondary amines Chemical group 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical class O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical class C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-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
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical class CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 abstract 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004069 aziridinyl group Chemical group 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical class CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Chemical class CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 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
- 150000003440 styrenes Chemical class 0.000 abstract 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
- C08F26/00—Homopolymers and 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F26/06—Homopolymers and 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Vinyl N-heterocyclic carbamates of the general formula <FORM:1116005/C3/1> in which -A is the residue obtainable by removing the hydrogen atom from a secondary amine group in the ring of an N-heterocyclic secondary amine may be polymerized alone or in admixture with one or more ethylenically unsaturated monomers copolymerizable therewith, such as another vinyl N-heterocyclic carbamate, styrene, substituted styrenes, vinyl acetate or butyrate, vinylidene chloride, acrylic or methacrylic acid, ethyl acrylate, methyl methacrylate, acrylonitrile, N-isopropyl acrylamide, ethylene, propylene or 1-butene. Polymerization may be effected in bulk or in solution in benzene in the presence of a catalyst such a ,a 1-azobis-(isobutyronitrile), hydrogen or benzoyl peroxide or potassium persulphate. Examples describe the production of homopolymers of vinyl N-piperidinyl-, vinyl N-pyrrolyl- and vinyl N-aziridinyl carbamates. Vinyl N-aziridinyl carbamate is said to polymerize through both the aziridine ring and the vinyl group.ALSO:Compounds having the general formula <FORM:1116005/C2/1> in which -A is the residue obtainable by removing the hydrogen atom from a secondary amine group in the ring of an N-heterocyclic secondary amine, are prepared by reacting a vinylhaloformate with a compound of the general formula HA in which A is as above. Examples describe the production of vinyl N-piperidinyl, vinyl N-pyrrolyl and vinyl N-aziridinyl carbamates by reacting vinyl chloroformate with piperidine, pyrrole and ethyleneimine respectively. The carbamates of the invention can be employed as odoriferous ingredients in deodorizers or as herbicides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB741166A GB1116005A (en) | 1966-02-21 | 1966-02-21 | Vinyl n-heterocyclic carbamates, process for their production and polymers thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB741166A GB1116005A (en) | 1966-02-21 | 1966-02-21 | Vinyl n-heterocyclic carbamates, process for their production and polymers thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1116005A true GB1116005A (en) | 1968-06-06 |
Family
ID=9832617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB741166A Expired GB1116005A (en) | 1966-02-21 | 1966-02-21 | Vinyl n-heterocyclic carbamates, process for their production and polymers thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1116005A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3274681B2 (en) | 1989-05-02 | 2002-04-15 | ボーシュ アンド ローム インコーポレイティド | New vinyl carbonate and vinyl carbamate contact lens material monomers |
| US8222200B2 (en) | 2003-04-14 | 2012-07-17 | Givaudan Sa | Organic compounds |
-
1966
- 1966-02-21 GB GB741166A patent/GB1116005A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3274681B2 (en) | 1989-05-02 | 2002-04-15 | ボーシュ アンド ローム インコーポレイティド | New vinyl carbonate and vinyl carbamate contact lens material monomers |
| US8222200B2 (en) | 2003-04-14 | 2012-07-17 | Givaudan Sa | Organic compounds |
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